


How To Be A Heartbreaker

by anythingbutplatonic



Category: Arrow (TV 2012)
Genre: Alcohol, Alternate Universe, Comedy, F/M, Fake/Pretend Relationship, Fluff, Olicity Fic Big Bang, Romance, Romantic Comedy
Language: English
Status: In-Progress
Published: 2015-12-19
Updated: 2016-03-07
Packaged: 2018-05-07 03:05:10
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 9
Words: 34,200
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5441111
Author URL: https://archiveofourown.org/users/anythingbutplatonic/pseuds/anythingbutplatonic
Summary: <blockquote class="userstuff">
              <p>AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.</p><p>Written for the Olicity Fic Bang 2015.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning.
> 
> [Listen to _How To Be A Heartbreaker:_ The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

**Playlist for this chapter:**

1.  _How To Be A Heartbreaker -_ Marina + The Diamonds

2.  _This Is How We Do -_ Katy Perry **  
**

3.  _Blame It_ \- Jamie Foxx ft. T-Pain

* * *

 

“Gather round, girls, it’s time for  _Truth or Dare_!”

The gaggle of women clustered around the coffee table in Felicity’s tiny apartment shrieked and giggled, jostling each other for a prime spot around the table as Sandra, the oldest (and tipsiest) of them, placed an empty wine bottle in the middle of it with a flourish.

Felicity herself, however, groaned in despair from her position on the couch, trying to hide her face behind one of the cushions. She  _hated_  “Truth or Dare”. She was too much of a prude by her own admittance to answer any of the “truth” questions, and too much of a chicken to do any of the “dares”.

Plus, she definitely hadn’t drunk enough wine to be able to do either, though her friends had certainly made up for her lack of intoxication, judging by their flushed cheeks and sparkling eyes.

Which were all now staring at her, five pairs of alcohol-glassy eyes in total, identical expressions of expectation on each of their faces.

Felicity loved her friends. Adored them, in fact.

She just really, really hated  _Truth or Dare_.

“C’mon guys, you know I don’t like  _Truth or Dare_ ”, she complained, when they wouldn’t stop staring at her in that hopeful, expectant way that very drunk people look at you when they want you to do something.

Really, it was a rather disturbing look. It made her feel like she was in a horror movie where the innocent young girl walks into a dusty old bedroom in a creepy abandoned house and finds rows and rows of porcelain dolls with frozen, staring eyes, just  _looking_  at her.

As it happened, Felicity also hated dolls. They creeped her out, with their plastic smiles and frilly dresses and weird, tiny hands, not to mention their hair, which she could never tell was real or not…

“Don’t be a spoilsport,” chirped McKenna, her sixth (seventh? eighth?) glass of wine dangerously close to tipping out of her hand. “It’s your last night of freedom! On Monday you join the rest of us in that wonderful capitalist institution that we call a nine-to-five job, with terrible pay and no overtime!”

“Hear, hear!” chorused the rest of her friends, sloppily clinking their glasses together.

Which reminded Felicity of why they were all here in the first place; they were celebrating her landing her very first adult job since graduating from MIT, as an IT consultant at Queen Consolidated, the biggest and wealthiest company in Starling City.

The Queen Consolidated that had been in the “Top 10” section of the Fortune 500 list for the last 15 years.

The Queen Consolidated that was owned by Robert Queen and his wife Moira, who were one of Starling City’s wealthiest elite couples, the one percent of the one percent, and second only to Malcolm and Rebecca Merlyn, who owned the city’s second wealthiest company, Merlyn Global.

The Queen Consolidated that was in line to be inherited by the Queens’ son Oliver, who was, quite frankly, the most attractive man that Felicity had ever seen.

At least, he looked handsome in all of the photographs that Felicity had seen of him in the entertainment pages of the newspapers and trashy magazines she devoured as a guilty pleasure each evening while she ate poptarts in bed.

Not that she made a habit of eating poptarts and staring at photographs of Starling City’s most eligible bachelor every night, like it was some creepy fetish thing.

She did not have an Oliver-Queen-and-poptarts fetish.

So, yes, it was  _that_  Queen Consolidated that, as of Monday, she would be working for.

“Okay, fine,” Felicity grumbled, amidst cheers from Sandra, McKenna, and Laurel, and some clapping from Sara and Carly. “I will play one round of  _Truth or Dare_. One. No more, and no less.”

She grabbed the mostly-empty bottle of wine nearest to her and poured herself a generous  measure. “Let’s get the humiliation over with.”

“Me first!” crowed Laurel, reaching over to give the bottle in the middle of the table a fierce spin. It landed on Carly, and this time, Felicity joined in with the cheers and whooping, glad that the bottle hadn’t chosen her as its first victim.

“So,” Laurel turned to Carly with a businesslike expression, sitting back on her knees and surveying her friend with a look that wouldn’t have been out of place in a courtroom, which was alarmingly fitting – Laurel, when she wasn’t dressed in a slinky red cocktail dress with an alcohol-fuelled wicked glint in her eye, was a lawyer. One of the best, in fact. Right now, however, her intention was to make Carly squirm, and so she asked the million-dollar question. “Truth or dare?”

“Truth,” Carly replied without missing a beat. Nothing ever fazed her, not even the threat of being made to spill her darkest secrets, and Felicity was a little jealous of her for it.

“When did you and Andy last have sex?”

Laurel pulled no punches; she went straight for the jugular, every time.

“Three days ago,” Carly said, with barely any hesitation; she took a gulp of wine and gave Laurel a triumphant smile. “You need to up your game, Lance.”

Carly spun the bottle, and it landed on McKenna, who looked rather afraid. Felicity didn’t blame her.

“McKenna, truth or dare?”

“Truth.”

They all crowded round to hear what horrible humiliation Carly would think up. She savoured the moment, swilling her wine in her glass, before her lips curled into an ominous smirk and she asked, “Was the last man you slept with circumcised or uncircumcised?”

 _I’m sensing a theme here_ , Felicity thought, feeling that knotting pit of dread in her stomach curl tighter, her nerves starting to jangle. The last man she’d been in a serious relationship with had been Ray Palmer, a sweet but eccentric grad student at MIT with a penchant for hyperbole and a lot of big ideas that never seemed to really work in practice. The last time she’d slept with anyone had been a month after their break-up.

McKenna grinned into her glass. “ _Un_ circumcised.”

 _I definitely need to be more drunk_ , Felicity thought, and she happily threw back two more glasses of wine as Sandra, Laurel, and then McKenna again were chosen by the Wine Bottle of Fate.

Then it was Laurel’s turn to spin again, and the bottle landed on Felicity.

She was incredibly grateful for the large amount of wine she’d consumed in the last half an hour when Laurel asked her, “Truth or dare?”

She would later curse the same amount of wine for being responsible for what she said next.

“Dare.”

Laurel sat in silence for a good few minutes, contemplating what she would ask her to do, then conferred in slurred whispers with McKenna, Sara, Carly and Sandra while Felicity awaited her fate. The alcohol in her veins was creating a pleasant, warm buzz under her skin and made her feel braver than she would ordinarily be feeling at this stage.

Laurel pulled her tablet out of her bag and spoke as she typed, surprisingly quickly for someone who was rather drunk and had the rosy cheeks to show it. “Alright, Felicity Smoak, we  _all_  dare you…”, she looked around at the others for their approval, which they gave, nodding enthusiastically, “…to seduce and date, for a minimum of one month, a man of our choice, that I will now find for you using the powers of the Internet.”

“ _What?_ ”

Felicity stared, eyes comically round, her mouth agape. Her friends had gone mad. They had actually gone mad. She couldn’t seduce a random stranger! Scratch that, she couldn’t  _date_  a random stranger, and she especially couldn’t date a random stranger on a drunken dare given to her by her drunk friends.

Could she?

“Nuh-uh, no take-backs,” McKenna said, seeing the look of apprehension on Felicity’s face. “You chose to do a dare, and now you have to do the dare, because that is the  _law_.”

Felicity groaned. “Just tell me who my mystery date is and get it over with before I agree to anything else.”

“Felicity Smoak, say hello to Mr. Right Now,” Laurel announced, flipping her tablet to show Felicity…

…a photograph of Oliver Queen, looking handsome as ever in a dark blue suit that brought out the intense colour of his eyes.

“You want me to seduce my  _boss_?” Felicity shrieked, the colour in her cheeks now only partly due to alcohol.

“No,” said Laurel mischievously, “I want you to give him a taste of his own medicine by making him fall in love with you,  _and propose_ , within exactly sixty days.”

_No._

_No way._

_No_ freaking _way._

She had intended to tell Laurel that she wasn’t going to do it. That there was absolutely no chance in Hell that she was going to agree to her  _insane_  plan that involved getting her (very handsome, very rich, and no doubt very  _charming_ ) boss to  _ask her to marry him_.

In sixty days.

_Was Laurel out of her mind?_

But what Felicity actually said was, in horrified disbelief, “Propose?”

“Yes,” Laurel confirmed. “Propose. Get his ring on your finger and then break his heart, and he’ll finally know what it’s like to get left at the altar, metaphorically speaking.”

“But,” Felicity stuttered, still not quite able to believe it, “you said I only had to date this person for a month! And he’s my  _boss_. Who I have to work with. And see. Every day. Because I work for him. Well, his parents. I work at his parents company and  _oh, my God, I can’t do this!_ ”

“You can,” said McKenna, gesturing enthusiastically with her glass, “and you will, with a little help from all of us. Think of it as a social experiment;  _How To Bring A Billionaire Playboy To His Knees_.” She winked. “In more ways than one.”

“Oh my God, McKenna!” Felicity hid her face in her hands.

“We should write about it!” chimed in Sandra, her face scarily animated in a way that made Felicity think that things were about to get even more insane. “Put up a blog, and write down everything that Felicity does, just like a real experiment.  _How To Be A Heartbreaker: One Woman’s Mission to Get Justice for Females Everywhere Who Have Been Used and Abused by Rich, Entitled Men._ ”

“And then, when you finally give him back the ring and confess that it was all a set-up, we’ll publish it and everyone will go  _crazy_  to find out how you did it,” added McKenna.

Felicity thought about what had been said so far. And then she thought about it some more. And the more she thought about it, the more it…made sense?

 _Oh God, she really was crazy_.

“Even if I did agree to this insane plan,” said Felicity, “and I am  _not_ , by the way – what makes you think that it would even work? I mean, we all know that I’m no pinup model, and that I’d rather write computer codes than do body shots off a hot male stripper’s ass on a Friday night. What makes you think I’m even his type?”

“Oh please,” snorted Carly, “ _woman_  is his type. Some lower necklines and brighter lipstick will have him  _gagging_  for you.”

Felicity thought about it for a third time, worrying her bottom lip between her teeth. It  _would_  be fun to get a bit of feminine revenge…but could she really lie to someone like that, pretend she cared about them when she didn’t and then break their heart so callously?

 _Yes,_ she thought. Or maybe it was the alcohol doing the thinking.

 _Screw ethics_ , _this is about female empowerment and finding out what Oliver Queen looks like with his clothes off._

“I’ll do it!” Felicity blurted, before she could change her mind.

Her girlfriends cheered, then immediately launched into a loud, enthusiastic discussion of the details of their plan. Felicity let their boisterous chatter wash over her, her mind running wild, already five steps ahead, while the others debated blog titles, hypothetical dates that Felicity and Oliver might go on, and how much they thought an engagement ring from a Queen would cost.

Dates. Engagement rings.  _A marriage proposal_.

She had just sixty days to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her.

Starting now.


	2. Chapter 2

**Summary for the Chapter:**

> AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.

**Notes for the Chapter:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning.
> 
> [Listen to _How To Be A Heartbreaker_ : The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

**Playlist for this chapter:**

1\. _1234_ \- Feist

2\. _Confident_  - Demi Lovato

_________________________________________________

 If Felicity had been nervous about starting her very first adult job before, she was _this close_ to shaking apart in her pastel-coloured pyjamas as she waited for a pot of coffee to brew now that she had an entirely different goal to fullfil.

Damn her friends, and their powers of drunken persuasion, to Hell and back.

Now, not only did she have to concentrate on not puking all over the brand-new shoes that she’d purchased for the occasion, she also had to exert enough confidence and feminine wiles to make her boss’s son look her way instead of at whichever tall, leggy brunette was his flavour of the month.

Which made it sound like he was trying out new chip flavours rather than just having a lot of sex.

Oh, God.

 _Sex_.

She’d completely forgotten about sex! If she was going to make Oliver fall in love with her, she was probably going to have to have sex with him at some point.

Sex with Oliver Queen. Any other time, she would have flushed with an embarrassing amount of desire at the thought, having fantasized about it enough times in the privacy of her own head. Now, however, the prospect was less arousing and more terrifying.

“Coffee, I need coffee,” she mumbled as she shook her head, trying to clear it of the alarming rate at which her thoughts were spiralling down a never-ending tunnel of panic which would result in her quitting her job before she’d even started. Why was her coffee maker taking so damn long to brew a single pot of coffee?

As soon as the high-pitched _beep_ signalled that it was ready, she slammed a chipped mug under the spout with more force than was probably necessary and tapped her foot anxiously on the linoleum floor as it filled, the rich aroma already making her feel a _little_ more sensible.

She took the mug into her bedroom, where she’d thrown open her closet the minute she’d rolled (reluctantly) out of bed in anticipation of the next Very Scary Thing she had to do that day.

_Choose what to wear._

Everything she owned suddenly felt inadequate. On one side of her closet were the dark skirts and sensible blouses she’d bought when she’d taken the job offer at Queen Consolidated, fully expecting the dress code to be strictly formal. IT consultants still had to look the part, after all. But in light of what lay ahead of her, they were more likely to make her look like she was going to a funeral instead of trying to woo a man.

It was at this very moment in time that Felicity wished her mother were here, which was a very scary thought indeed, because if she wanted advice from her mother then the situation really must be desperate.

Donna Smoak was a strictly dress-and-high-heels woman, her long hair always immaculately curled, lipstick perfect and false eyelashes fluttering. When it came to clothes, she preferred them short and bright and showing lots of cleavage. And she got plenty of attention from men.

Felicity was nothing like her, and as much as she adored her mother, she was grateful for that fact. Her mom could be…a lot to handle. But now she wished they were a little more alike, because it’d make everything a lot easier. Her mom would know what to do; she’d know what shade of lipstick she should wear, and how short her skirt should be, and how to style her hair in just the right way to emphasize the shine and colour and make anyone who passed her on the street do a double-take.

But calling her mom would mean having to explain to her exactly _why_ she wanted to know how fine the line was between “come hither” and “my second job is walking the streets” when it came to skirt length, and she really didn’t want to do that.

So, she was back at square one.

A glance at the baby-blue vintage alarm clock on the nightstand behind her also told her that she was _late_.

She gulped the rest of her coffee frantically as she pulled a brush through her tangled hair one-handed, then left the empty mug on her bedroom floor while she brushed her teeth, all the while thinking, _Crap, crap, crap_.

She hadn’t eaten breakfast. She didn’t have time.

She _couldn’t_ be late on her first day.

Thrusting her arm blindly into her closet, she pulled out a bright purple calf-length skirt and the first white shirt she found, which happened to be a sleeveless blouse with a Peter Pan collar.

Simple, but hopefully effective.

Felicity tried not to think too much as she dressed quickly, smoothed her hair – it would have to stay loose and wavy on her shoulders, there was no time to pull it into a ponytail the way she normally would – and put on her glasses.

Then took them off again as she remembered that she wasn’t wearing any make-up.

It was 8:31am. Queen Consolidated was twenty minutes from her apartment. If she left right now, she would only be five minutes late.

They wouldn’t fire her for that, would they?

Ten minutes later, she threw herself into her car and prayed that she didn’t get caught at a red light, because she was now _really, really_ late and didn’t want to be, well, _later_.

Felicity Smoak: Late On The First Day Of Her New Job Girl.

It was a mouthful, but it had a certain straightforwardness about it. She only hoped that it didn’t catch on.

***

During her 11:15am coffee break – though, considering her late arrival, she didn’t really felt like she deserved one, since she’d only been at her desk for an hour and a half - she switched on her cellphone to find a text from Laurel.

**From: Laurel Lance (11:01am)**

_Seen Mr. Right yet? :)_

By “Mr. Right”, of course, she meant Oliver. Felicity didn’t really appreciate her friend’s attempt at a joke. She was taking this far too lightly for someone who was usually so serious.

She texted her back.

**From: Felicity Smoak (11:16am)**

_No. Shouldn’t you be working?_

A few minutes later, she received a reply.

**From: Laurel Lance (11:19am)**

_It’s a slow day. Lots of paperwork to get through._

**From: Felicity Smoak (11:20am)**

_So you thought you’d harass me instead?_

**From: Laurel Lance (11:24am)**

_It’s not harassment, it’s keeping a close eye on the subject of the experiment. You’re not backing out, are you? Because once you agree to a dare, you have to go through with it. ALL OF IT._

Felicity sighed and took a long gulp of coffee.

**From: Felicity Smoak (11:26am)**

_No, I’m not backing out._

**From: Laurel Lance (11:27am)**

_Then why haven’t you made a move yet?_

**From: Felicity Smoak (11:29am)**

_Because I’ve only been on the job for an hour and a half and I was already twenty minutes late this morning. I can’t spend all day wandering around Queen Consolidated hoping I’ll bump into Oliver. I’d be fired for sexual harassment._

**From: Laurel Lance (11:31am)**

_Somehow I doubt he’d mind much._

Felicity choked on the sip of coffee she had been about to take; she didn’t want to think about _that_ right now. She wasn’t going to be the creepy employee who followed her boss around making goo-goo eyes at him and dropping not-so-subtle compliments about the size of his biceps. And then asking if she could _feel_ his biceps.

 _No_. She was _not_ going to be that person. If she was going to go along with Laurel’s insane plan to seduce Oliver Queen and then throw him out on his ass, she was going to do it the right way. The _respectable_ way. Which meant absolutely zero stalking, of any kind.

She wouldn’t go to him. She would make him come to her.

As she finished the last dregs of her coffee, a plan started forming in her mind…

 ***

“No, it needs to be lower.”

“What? Any lower and she’ll be arrested for streetwalking! _This_ is classy, and sexy. She’s trying to trap Oliver Queen, not get a job as a showgirl in Vegas.”

“My Mom used to be a showgirl,” Felicity interjected, cutting off Sara and Carly’s squabbling. “I’ve seen what some of them wear, and _this_ ,” she plucked at the fabric of the dress she was currently wearing, “is definitely tame compared to that.”

“Yay!” Carly squealed, clapping her hands together. She stuck her tongue out at Sara. “Told you.”

The front door opened and Laurel appeared, looking harried, her hair windswept into brown tangles. She was still wearing her pale grey “court suit” and had a large, thick briefcase tucked under one arm.

Sara pointed at her older sister. “You,” she accused, “are late.”

“Court ran late. I didn’t have time to go home and change.” She dumped her briefcase on the coffee table and immediately sank onto Felicity’s couch to take off her shoes, groaning with relief as she wiggled her toes experimentally, glad to be rid of the four-inch heels she wore whenever she had to appear in court. It made Felicity’s own feet ache just looking at them. “So what are we doing here?”

“Felicity had an _excellent_ idea for how to approach our target without looking like the office stalker,” Carly said.

“I was doing some research during lunch today. The first Friday of every month, the Queen family host a fundraising gala at their mansion for a charity of their choice. This month it’s a charity that helps to tackle homelessness in the Glades,” Felicity explained. “Usually, these things are only for other really rich people, but I checked – any employee of Queen Consolidated is automatically invited to the gala, no matter what they do or which department they work in. My plan – and I think it’s a very good one, even if I _do_ say so myself – is to show up at the gala, introduce myself to Oliver that way, and then he’ll know who I am _and_ I don’t have to risk a sexual harassment suit.”

Laurel considered this for a moment. Then she smiled. “I like it. It’s simple, straightforward, and it’ll get you noticed, which is what we want. Is that what you’re wearing?”

Felicity looked down at herself, at the sapphire-blue silk gown she was currently trying on for the approval of her friends. It was the most luxurious – and most expensive – item of clothing she owned, and she had only worn it a handful of times. “It’s the fanciest thing I own. It’s practically new. Do you think it’s too much?”

“Not at all,” Laurel said. “I think it’s perfect. But I have something that I think might just take it over the edge….”

***

The rest of the week passed by in a fairly uneventful way.

Felicity wasn’t late again, much to her relief, and she was far too preoccupied with the demands of her new job to think about much else except work and what kind of take-out she would order for dinner each night. Cooking had never been her strong suit, and most days she crashed into her apartment before 7pm at the earliest, exhausted from the day and desperate to change into old, comfortable pyjamas and eat greasy fast food while flicking through her Netflix queue.

Who knew that being a simple IT consultant would be so _draining_?

If she wasn’t filing paperwork or updating employee details on the company database – pretty routine stuff, but time consuming, even when her typing speed _did_ exceed most people’s maximum even on an off-day – she was taking calls from other departments that needed IT-related things done, or else dealing with personal requests from her fellow employees.

All of this, she did while fielding texts from Laurel and Sara and Carly and McKenna and Sandra about whether or not she’d seen “the subject” yet.

During a brief lull in her daily activities on Wednesday afternoon, she had such an exchange with Laurel.

**From: Felicity Smoak (2:14pm)**

_I really wish you’d stop calling him “the subject”_. _He’s a person, not a lab rat_.

**From: Laurel Lance (2:16pm)**

_A sexy, sexy lab rat._

Felicity had resisted the very strong urge to slam her forehead into her desk.

And when she wasn’t thinking about work or watching endless episodes of _Say Yes To The Dress_ while eating her way through her second carton of Cambodian beef and noodles, she was worrying about her Grand Plan to show up at the Queen family charity gala and leave Oliver swooning at her heels.

Which would be less of a problem if the gala wasn’t being held in _five days_.

Adding to her worries was the fact that she was already down to fifty-two days out of her designated sixty in which to enact her feminine charms and get Oliver to propose, and she would be lying if she said that the rapidly-narrowing time frame wasn’t beginning to bother her.

 _Why_ had she agreed to this, again?

Ah, yes, she remembered with a grimace. _Alcohol_. That, and Laurel’s powers of persuasion which, Felicity thought, had to be cheating somewhat because you weren’t supposed to use lawyer tactics on your own friends.

“Aaaaargh!” Felicity buried her face into one of the couch cushions and let out a noise of frustration. There _had_ to be an easier way to approach this. Something simple, something she hadn’t thought of yet.

The genius-level IQ had to kick in _some_ time. Maybe her prestigious MIT degree would more than simply overqualify her for her current job yet.

Tired and frustrated, she switched off her TV and dumped her empty bowl of ice-cream in the sink. Tomorrow, she would be down to fifty-one days. And after Friday, it would be forty-three.

“How on earth am I going to pull this off?” she asked to the open space of her empty kitchen, running her hands through her hair distractedly.

Bed. Bed and sleep. That’s what she needed. Tomorrow was another day.


	3. Chapter 3

**Summary for the Chapter:**

> AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.

**Notes for the Chapter:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning.
> 
> [Listen to _How To Be A Heartbreaker:_ The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

 

 

 

* * *

 

**Playlist for this chapter:**

1\. _Tongue Tied_  - Grouplove

2\. _White Light_  - Shura

3\. _Up Up And Away_ \- Kid Cudi

* * *

 

**CHAPTER 3.**

“Miss Smoak!”

Felicity didn’t immediately recognize the voice that called out to her just as she was about to press the button on the elevator to take her back down to the IT department; she jumped, whirling round in the direction of the voice, and found herself face-to-face with Walter Steele, Queen Consolidated’s Vice President. He was a tall man, bald, with kind eyes and a no-nonsense approach to business, or so she’d heard.

And, it seemed, he wanted to speak to her.

“Is everything okay?” Felicity clutched the stack of folders she was carrying tighter to her chest, suddenly nervous. She’d only been working at the company for just over a week. She thought she’d been doing a pretty good job. 

He wasn’t going to _fire_ her, was he?

“Of course. In fact, everything is more than okay. Your supervisor tells me that you’ve made quite the impression on the IT department since you began working here a week ago.”

Felicity almost dropped her stack of folders in surprise. “He did?”

Walter – Mr. Steele? – smiled. “He spoke very highly of you. And after reviewing your progress over the last seven days, I have to agree with him. You’re a very talented young woman, Miss Smoak. I suggest you continue working to the high standards you’ve been reaching so far. Queen Consolidated is very lucky to have you.”

“Th-thank you,” she stammered, too shocked to say much of anything else. “Sir!” she added quickly. “Thank you, Sir.”

“Please, call me Mr. Steele.”

Felicity nodded. “Thank you, Mr. Steele.”

The elevator pinged, announcing its arrival, and Felicity was glad for the distraction – and the reminder that she was, in fact, an employee and that she should probably get back to work. The information held on Queen Consolidated’s mainframe wouldn’t back up itself.

She freed one hand and pointed needlessly in the direction of the elevator. “I should probably get back to work.”

“And so should I. It was nice to speak with you, Miss Smoak. Keep up the good work.”

Mr. Steele gave one final smile and then was moving past her down the corridor with a purposeful stride, what were probably very expensive shoes squeaking on the polished floor with each step. She wondered what it would be like to own shoes that expensive, shoes so shiny you could see your own face in them when you put them on in the morning.

The last time she bought a pair of shoes _that_ expensive was when her mother had all but forced her to do so for a cousin’s wedding. They were still in the box at the back of her closet, only worn once.

And anyway, she preferred her favourite panda flats to the skyscrapers that her mother wore.

Consumed as she was by her own musings on expensive shoes and just how Donna Smoak had managed to work twelve-hour shifts seven days a week in six-inch heels (and wondering whether she gave her mom enough credit for doing so), she didn’t realize that the elevator had closed again. Mentally slapping herself for getting wrapped up in her own thoughts, she adjusted the stack of folders in her arms and listened to the elevator trundling off to pick up whoever had called for it from floor 43. She would simply have to catch it on its way back down.

Which, apparently, was nowhere near fast enough for an elevator belonging to one of the biggest and wealthiest companies in the tristate area, because it seemed to be taking its sweet time getting to her.

How long did it usually take for an elevator to travel thirty or so floors?

Patience had never been her strong suit, and she was starting to worry about being caught _not_ at her desk if her supervisor decided to check up on what she was up to. Glowing praise or not, her absence would surely be considered a black mark against her record.

Huffing impatiently, she shifted her weight from one foot to the other, watching as the glowing red numbers above the elevator counted down.

36…..35….34…..33…..32….31….

Lunch was in an hour. She was starving, and thinking about the bagel and her Thermos of coffee waiting for her back at her desk made her stomach rumble.

29….28….27…..26….25….

At least Laurel hadn’t bombarded her with texts about Oliver yet today. Hopefully she would get the hint and stop trying to make Felicity even more nervous than she already was about this whole thing.

22….21….20…..19…..18…

She really, really wanted that bagel.

16….15….14….13.

_Finally!_

Much to her relief, the elevator gave a short _ding_ and the doors slid open. Felicity made a mental note to let building maintenance know how slow the elevators in this place actually were as she gratefully climbed into it, hoping her supervisor wouldn’t do his usual spot-check of the department before she reached her desk again.

She moved to press the button marked _7_ for the IT Department before she realized that she wasn’t alone.

And promptly bit through her tongue so hard that she tasted blood – which, _ow_ , that was definitely going to hurt for a while and also, _gross_ \- when she recognized the tall, grey-suited man currently lounging against the far wall of the elevator across from her as if a) he did this every day and b) he was very, very bored.

And oh, how handsome he looked.

Really, the photographs didn’t do him justice at all. She’d never understood meaning behind the phrase _a sight for sore eyes_ until she’d clapped eyes on Oliver Queen in the flesh, standing across from her in an elevator in that damn pale grey suit that brought out the golden colour of his hair and emphasized the regal set to his features, which was fitting, really, considering his surname was Queen.

She wondered if all the Queens looked like royalty in real life, or whether it was a coincidence that his family name matched his looks.

“It helps if you press the button for the floor you want,” Oliver drawled, looking up from his phone to raise an eyebrow at her. She’d always wanted to be able to do that. Raise one of her eyebrows, that is. Somehow she’d never managed it. “That’s what makes the elevator move.”

His tone was sarcastic, but his voice was playful. Almost melodic. Like he was baiting her.

“I know that!” Felicity blurted, and maybe her voice was a little higher-pitched than normal. “Of course I know how elevators work. I went to MIT. I’m _smart_. Very, very smart. Ergo, I know how elevators work.”

“Ergo?” Oliver repeated, and he was smiling. He’d put his phone away in favour of looking directly at her, crossing his arms in front of him like he had all the time in the world.

Because the elevator wasn’t moving. Right. Because she hadn’t pressed the button yet.

Because she’d been so distracted by the sudden appearance of the man she’d gone all week trying to avoid so that she _didn’t_ make a fool of herself when they eventually did meet, that she’d momentarily forgotten how elevators work. 

_Great first impression, Smoak. Now you’ll_ definitely _get him to propose in sixty days._

“Yes,” Felicity said, a little breathless, and her tongue sore from where she’d bitten it. “Ergo. Now if you don’t mind,” she continued, standing up a little straighter and pretending to be more confident than she felt, “I have to get to work, so I’m going to press the button for the IT Department now. That’s number seven. I mean, obviously, you know it’s number seven, it’s your company. Well, your father’s company, but you must come here every day, being the boss’s son and all, so you know your way around. Obviously.”

Oliver’s smile widened. Was it just her imagination, or did he look….curious?

“Obviously,” he nodded, and even from this distance, she could see the mirth – or maybe it was amusement, at the babbling stranger he was stuck in an elevator with – in his eyes, and the dimple in his left cheek. It made him look youthful, carefree, at odds with the sharpness of his clothes and the high polish of his shoes. A young boy’s face on the body of an older, more experienced man.

“I’m sorry,” she blustered, “you’re probably a very busy man. And I’m a very busy woman. So I’ll just,” Felicity pointed in the direction of the bank of buttons built into the elevator wall, “press this button right here,” she pressed the number marked 7, “and we’ll just ride down in silence. Starting now. No more talking from me. You can be sure of _that._ ”

As the elevator finally rumbled into life, the doors sliding closed and they began their descent, a tense silence filled the space. Felicity was very aware of Oliver’s eyes on her, his presence in the elevator making her nervous. His wide, broad-shouldered body took up too much space for her liking; it made her uncomfortable, knowing that he was there and that she’d made a fool of herself in front of him.

She wondered what he was thinking.

She dared glance at him through her peripheral vision, and saw that he was engrossed in his phone again. Texting, by the looks of things, strong fingers darting over the keypad in fast movements. A girlfriend, probably. No, not a girlfriend. A date. A hook-up. Maybe more than one.

She tried not to think about the kinds of women he would be speaking to. The kinds of women she would have to compete with for his attention.

When the elevator arrived at her floor, and she was greeted by the sight of the IT Department at last, she could have wept with relief. She all but ran out in her hurry to get as far away from Oliver and his stupidly cute cheek dimple as possible, clutching her stack of folders to her chest and praying that she didn’t have dark circles under her arms from any nervous sweating, because she hadn’t thought to bring a fresh shirt with her.

Patting down her skirt with her free hand where it had gotten rumpled, she gratefully exited the elevator and left Oliver Queen behind, only the ache in her tongue reminding her that the embarrassing exchange had happened at all.

Which wasn’t helped by the fact that, minutes later, she was hissing in pain again as she burned it on her too-hot coffee when she eventually got to her desk.

 ***

Oliver Queen was a man in demand; that much was obvious to anyone who bothered to watch the news or read a newspaper. The eldest of the Queen offspring grabbed headlines and made them what they were, and the satisfaction of having his exploits splashed across the entertainment news pages was one of the things in life he really did enjoy.

One of the things he didn’t care for, however, was being forced to show his face at his father’s company and paraded around like a show dog in the hope that acquainting himself with the business world would make him more comfortable with the idea of taking on the CEO position at Queen Consolidated once Robert Queen retired.

Which was, for all intents and purposes, something that Oliver had no interest in doing whatsoever.

He didn’t want to be CEO of Queen Consolidated. He didn’t want to be CEO of any company, period. He had little aptitude for business and even less for the corporate culture that came with it which, for as long as he could remember, had been sucking the life out of his parents’ marriage like water down the drain.

And the older he got, the more his parents tried to shoehorn him into the role that was carved out for him the moment they discovered that their first child was a boy.

Oliver hated it. So he rebelled against it, in any way he could think of it.  

Unfortunately, instead of them backing off, it only made his parents come down harder, which was why he’d been summoned by his dad to the QC offices for a “tour of the company”. It was meant to be a wake-up a call, a hopeful attempt at encouraging Oliver to accept his place in what would eventually become his domain.

That hopefulness had lasted all of ten minutes before Oliver had been overcome with the desire to launch himself out of his father’s fiftieth-floor window along with the plush-seated pristine leather chair he’d been sat in.

To call the visit unsuccessful would therefore be an underestimation, as Oliver had no more desire to become CEO as he made his way back down to the front entrance than he did when he’d met with his father four hours ago.

And, as if his day couldn’t possibly get any more tedious, he remembered with only half an hour to spare that he was supposed to meet his mother for lunch at a fancy Japanese restaurant a few blocks from the QC building, which was really just an excuse for her to grill him about that morning’s events.

For someone who was closer to thirty than twenty, his parents often still treated him like a naughty child who only needed a firm hand to bring them into line. He was a grown man; he made his own decisions. Just because they weren’t the decisions his parents wanted him to make, didn’t mean he needed disciplining like a misbehaving toddler.

He wondered if had the courage to blow off his mother and skip the judgemental looks in favour of doing….well, literally anything else.

And then, Life had given him a distraction, in the form of a petite blonde woman in red-framed glasses who’d hurried into the elevator on the thirteenth floor and did a poor job of hiding the fact that she’d bitten her tongue in surprise when she’d noticed who was sharing the space with her.

Oliver had to admit that he was flattered by that.

She was cute, unbelievably so, almost conservative in the white blouse and bright skirt she wore, and she attracted his attention purely because she was different from his usual type of woman. If she worked at QC, then she must be intelligent. Hardworking, too, and proud.

_Definitely_ not his usual type.

And yet - there was…. _something_ about her that made him stop for a moment and actually think about something other than the immediacy of physical attraction, a drunk hook-up in a club, a one-night-stand at the Four Seasons.

But she worked for his father’s company. That made her off-limits.

Still, there was no harm in teasing her a little.

“It helps if you press the button for the floor you want,” he’d told her, pretending to be engrossed in his cellphone. Pretending, because he only needed her to _think_ that he was busy. Make yourself unavailable, and they’ll only want you more. It worked every time. “That’s what makes the elevator move.”

Cute Elevator Girl babbled, letting him know that she had been to MIT and therefore knew exactly how elevators worked, because she was smart. Emphasis on the _smart_.

Cute Elevator Girl was even cuter than he’d first thought.

_You can’t date someone involved in your father’s company_ , he reminded himself. _Not unless you want to be accused of sexual harassment if it ends badly_.

Then the elevator stopped, and the doors slid open, and Cute Elevator Girl hurried out, her blonde ponytail bobbing as she walked. His eyes followed her hand as she nervously patted down her skirt, drawing his attention to her round ass and shapely hips, and the muscles in her legs. Her nails were painted aquamarine and matched the studs in her ears.  

He watched her walk away and felt genuinely disappointed that he couldn’t leave with her, but instead had to travel down the rest of the way to the lobby, then out through the front doors, and onto a lunch date with his mother that he hoped beyond hope would not end with him wanting to stab himself in the eye with a chopstick.

 ***

“Tommy! Stop whatever it is you’re doing, I need your advice.”

Tommy Merlyn had dealt with his best friend’s theatrics for over two decades, but that didn’t stop him from jumping out of his skin at the sound of Oliver’s voice as he breezed into the club, announcing his presence the same way he always did – with a flair for the dramatic and clearly no concern whatsoever for Tommy’s health.

“One of these days, you’re gonna give me heart attack if you don’t start announcing yourself a little more _quietly_ ,” Tommy said pointedly, pushing aside the papers he’d been rifling through to turn in Oliver’s direction. “I’m too pretty to die, Ollie.”

“Yeah, you wish,” Oliver teased with a grin as he braced himself against the bar. “You got any decent booze here?”

This brought Tommy up short somewhat, and he frowned while keeping his tone light. “Uh, _one_ , this is a nightclub so _obviously_ there’s booze here and, _two_ , it’s four in the afternoon. What do you need alcohol at four in the afternoon for?”

“If you’re seriously asking me that question, then you obviously don’t know me as well as you think you do,” Oliver replied, and the sarcasm in his voice betrayed the bravado he’d shown just moments earlier.

“Wait, this isn’t about your dad, is it? Because you know, we’re both in the same situation when it comes to overbearing asshole fathers so I can’t really help you with that.”

“No,” Oliver said. “Not my father. My _mother_.”

At that, Tommy winced. “Ouch. Maybe you _should_ be drinking at 4pm. Wait a second,” he said, coming around the bar to one of the small freezers along the back wall. He crouched and pulled out a bottle of vodka, frosted and steaming from the icy temperature, before reaching under the bar and pulling out two shot glasses.

“Here,” he said, pushing the bottle and one of the glasses in Oliver’s direction. “I’m all ears. _The doctor is in_ ,” he grinned, doing his best impression of what he imaged a therapist would sound like.

“My dad backed out of hosting the fundraising gala with her this Friday and she wants me to fill in for him. _Me_ , Tommy. As if I’m a suitable replacement for my father,” Oliver snorted, pouring a generous measure of vodka into his glass. He paused before continuing. “I don’t get why she can’t get Thea to do it. She’s better at it than me, and she actually _likes_ these stupid things.”

“Oh, I don’t know, Ollie – lots of alcohol, rich, attractive _older_ women vying for your attention….,” Tommy trailed off, shrugging. “Doesn’t sound that bad to me.”

“Then _you_ go,” Oliver said, with more bitterness than he would have liked, and immediately felt bad when Tommy recoiled from the acid in his tone, throwing up his hands in a gesture of surrender.

“Woah, dude, I’m just pointing out that this gala? Doesn’t have to be all bad. Get moderately drunk, invite a rich old lady up to one of the _many_ empty bedrooms in that ridiculously big house of yours, and the chances are you’ll get laid _and_ whatever charity it is you’re fundraising for will get a generous check courtesy of some spinster being shown a good time by a very attentive host. It’s a win-win, man.”

“I don’t need a cougar, Tommy.”

“Whatever. Look, if you really don’t wanna go to this thing, at least make it a little more bearable by inviting a hot date. Your Mom did tell you to bring a plus one, right?”

For the first time since he’d arrived, Oliver smiled, raising his glass to his lips. “Oh yeah,” he said. Before he could stop it, the image of the small blonde from the elevator flashed across his mind; he pushed it down. _Definitely not_. He downed the shot in one gulp, relishing the burn of the alcohol at the back of his throat. “She did.”


	4. Chapter 4

**Summary for the Chapter:**

> AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.

**Notes for the Chapter:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning.
> 
> [Listen to _How To Be A Heartbreaker_ : The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

* * *

  **Playlist for this chapter:**

1\. _Young Blood_  - The Naked and Famous

2\. _Hide Away_  - Daya

* * *

 

“We’re all set!” crowed McKenna happily as she turned her laptop around to face the others. They had gathered in Felicity’s apartment – God only knew why, her apartment was tiny and could barely fit herself, never mind the six people currently in it – for the official launch of Operation Heartbreaker, or so Sara had christened it, when she’d broken the news that she had, at last, come face-to-face with the unwitting Mr. Queen himself the previous day.

(To preserve some semblance of dignity, she left out the part where she almost bit half her tongue off.)

Now that “first contact” had happened, explained her friends, they could get down to the real business of their plan.

And that meant, apparently, starting a blog.

Felicity had never had much interest in blogging. She’d never had the time and, anyway, she didn’t think she’d have anything particularly interesting to say. Her life revolved around coffee, databases, writing code, and updating the Queen Consolidated company mainframe. When she wasn’t doing that, she watched Netflix, ate too much ice-cream, and avoided her mother’s phone calls.

Plus, the whole “strangers having access to every single aspect of your private life” thing? _Creepy_. And just plain weird. Who wanted to know what kind of salad you had for lunch? Who really cared? The idea of broadcasting the inner details of her everyday life on the Internet for the whole world to see wasn’t something she was really all that comfortable with. She didn’t even have a Twitter account.

 But apparently, a blog was what she was getting, although Laurel had pointed out that it wasn’t just for her. It was for _all_ of them, for the experiment. They would all take in turns updating it, while Felicity was busy wooing her target.

“Wooing?” Felicity had asked, wary. “I don’t woo. At all. I don’t even know _how_ to woo.”

“Yes, you do,” Sara had replied firmly. “At least for the next sixty days. You’ll learn.” She gave what she probably thought was an encouraging smile, but Felicity didn’t feel very encouraged.

Maybe she _should_ mention the whole “almost biting off her tongue” thing.

“Actually, it’s fifty days,” Felicity supplied, making her assembled friends whip their heads in her direction. “And after the gala this Friday, it’s forty-three.”

“Then we _really_ need to get started,” Laurel said, unruffled as usual. “How’s the blog coming along?”

“Almost there,” McKenna said, not taking her eyes off the screen of her laptop as she tapped furiously on the keyboard. “It’s nothing special right now, but it’ll get us set-up for the next fifty days alright.”

Five minutes later, McKenna had set up a webpage for recording the details of their exploits, and was now proudly showing it to the rest of the group.  

“Like I said, it’s nothing professional,” McKenna explained, throwing a wink in Felicity’s direction, “but we can fix that later.”

Felicity stared. And then stared some more, blinking behind her glasses as she tried to comprehend what she was actually looking at.

“It’s very….pink,” was what she eventually said, after a few moments.

Because it _was_ pink.

Bright, hot pink.

The kind of pink her mom liked to wear when she went grocery shopping, “just in case”.

_That_ kind of pink.

McKenna, however, didn’t seem to notice her chagrin. “Exactly! It’s supposed to be bit of girly fun, y’know, girl power and all of that. It’s what we agreed, remember?”

Felicity _did_ remember. Vaguely. Somewhere at the back of her mind. But maybe it was wise to just let her friends take the reins on this one.

“You’re still nervous about all of this, aren’t you?” Sara asked, her blue eyes full of sympathy.

“Yeah, I guess I am,” Felicity admitted quietly, staring at her hands where she folded them in her lap. Her nails were turquoise at the minute, but she would have to paint them a different colour for the gala. Cobalt, to match her dress; or maybe an understated nude, to provide a contrast with the deep colour of the gown. And silver jewellery was a must, to pick out the shine in her hair that her mom was always telling her she had.

Why did it all feel like more of a chore than an exciting game?

_Because you don’t think you can pull this off_ , her brain supplied for her. _You’re out of your depth and you’re not even sure any of this will work._

Felicity sighed. “I’m just not the right girl for this. Or him. I work in _IT_ , for God’s sake! I dye my hair! I have pyjamas with cupcakes on them!” She plucked at the strap of her bra underneath her shirt. “I haven’t washed this bra in two weeks!”

“At least you wear one,” Sara shrugged. “Most of the women that Oliver’s hooked up with probably don’t. Distracts from the nipple action,” she clarified, when the others looked confused.

“I don’t even wanna know how you know that,” Felicity grimaced. “But _look_ at me, guys! I’m just – I’m not his type. It’s not gonna _work_. He’ll figure out that I’m scamming him and leave before I get the chance to actually do anything, or he won’t be interested in me _at all_ and the whole thing will blow up in my face.”

“The gala is in four days, right?” Laurel said. “So focus on that. Concentrate on making an impression. Get him to notice you, and the rest will happen on its own. _Make him want to get to know you_.”

“And how do I do that without making a fool of myself?” Felicity asked, unable to keep the sarcasm out of her voice.

“You stand out from the crowd,” Sara said simply. There was a wicked gleam in her eye that made Felicity both feel nervous and reassured. Out of all her friends, Sara was the one who understood her best.

If she believed that she could pull this off, then maybe Felicity could, too.

Trying to shake off her nerves, Felicity tightened her ponytail and adjusted her glasses.

“So where do I start?”

***

“Now, what’s a beautiful woman like you doing in a place like this?”

Laurel looked up from her drink as none other than Tommy Merlyn approached her at the bar, grinning from ear to ear. The music was loud, but she heard him perfectly.

“Don’t you own this club?” Laurel retorted, gesturing with her glass at the dancefloor, currently packed with people. She took no notice of them, however; her eyes were on Tommy, and Tommy alone. She surveyed the room without really seeing anybody, the music just background noise to the sound of his voice.

If it were possible, Tommy’s grin widened.  “I do. And I didn’t think this was your scene, hence my surprise at finding you here.”

Laurel put down her drink, turning to face him with a lawyerlike expression. “And what kind of scene _do_ you think I have, Merlyn?”

“Oh, I don’t know,” Tommy said nonchalantly, pretending to look around the room at his numerous clientele before answering. “In your pyjamas in front of the TV, reading a case file with something playing on Netflix that you’re not really watching?”

That made Laurel pause. Because not only did it sting that he assumed she had no life outside the courthouse – which she did _not_ , she had plenty of fun – but also because he had, quite accurately, described her last Saturday night.

But he didn’t need to know that.

“Aha!” Tommy expostulated in the silence. “I was right.”

If he had had a drink in his hand, he would have taken a sip of it for dramatic effect. As it was, Laurel took a sip of her own drink to avoid answering him, but her eyes were hooded over the rim of her glass and he knew he’d caught her interest.

It was a _thing_ , between him and her. He flirted, she pretended she wasn’t interested, he flirted some more, she pretended harder….which only left him doing even more to get her attention, and eventually, she cracked.

If he were Superman, then Laurel Lance would be his Kryptonite.

“You know, you can flirt with me all you want, I’m still not going to agree to go out with you,” Laurel said, after a few beats, the _thump thump thump_ of the music vibrating in their ears. “So you can keep trying, but _this_ ….” She gestured to herself, to her hips and thighs and, yes, her breasts, which rose above the neckline of her dress in a _very_ tempting amount of cleavage, “is off limits to you.”

Tommy put his hands up in mock surrender. “Okay, okay, you’ve made your point. But at least let me buy you another drink and _then_ , I promise, I will leave you to your own devices.”

Laurel drained her glass and put it, empty, back on the bar.

One drink was allowed, wasn’t it?

Even if it was from _Tommy Merlyn_ , the heir to Merlyn Global Group, the man who had been pursuing her for the last three months, ever since she’d been assigned to case involving a sexual harassment suit filed by an MG employee against her superior?

Even if Tommy was the best friend of the man she was conspiring to seduce into a fake relationship with one of _her_ closest friends?

Laurel held up a finger. “Fine. One drink. But that is _all_.”

Grinning, Tommy signalled for the bartender to bring her a refill.

 ***

On Wednesday morning, QC’s personal mailman, a tall man with a shock of dark hair and bitten-down fingernails, came by the IT Department to deliver a stack of small white envelopes to every employee.

He dropped one on Felicity’s desk while she was engrossed in analysing the data on her screen, and at first she didn’t notice, because she _never_ got mail delivered to her desk. But the corner of the envelope caught her bare arm when she moved to click something on the screen and her curiosity was piqued.

The front was blank, no name or personal address of any kind. So it wasn’t private correspondence, then. Not a postcard from her mom, filled with as many questions as one person could fit onto one small square of paper (Donna was an inquisitive woman, to put it mildly), or some kind of love letter from a secret admirer.

Which, y’know. A bit disappointing. Not that she’d been working at QC long enough for anyone to _be_ her secret admirer, but one could sometimes hope….

Peeking around the edge of her cubicle to make sure that her supervisor wasn’t lurking somewhere to yell at her for not doing her job, she quickly assessed the (lack of) potential of someone seeing her not working before turning back to the envelope. It was thick, good quality brilliant-white cardstock, completely plain. There seemed to be a single piece of paper in it, also made of the same thick, high-quality material.  

Quickly, she pulled it from the envelope and unfolded it, smoothing it down against the flat surface of her desk to read it.

It was an invitation.

To the charity gala being held by Queen Consolidated that very Friday.

The same charity gala she was already planning on attending anyway so as to enact the next phase of The Plan To Make Oliver Queen Fall In Love With Her (or so she referred to it in her own head).

TPTMOQFILWH, for short.

Never mind the fact that even the acronym itself was far too long.

_Well, now at least it’s official_ , she thought to herself. _My fate is sealed. My destiny has been foretold. Who needs crystal balls, anyway?_

This was actually happening.

This was _actually happening_.

Commence Phase Two.

 ***

“Speedy!”

Oliver caught hold of his younger sister just as she was going past the open door of his bedroom; she reached the end of the hallway and turned back a few paces, folding her arms in front of her chest.

“How many times have I told you not to call me that?” she asked petulantly, shaking her short brown hair away from her face. “I’m seventeen, not seven.”

Oliver stepped into the hallway, leaning against the frame of his door. “Aw, c’mon. You know you secretly love it.”

“I don’t.”

The argument was one they’d had a hundred times before; ever since Thea had decided she was too old for her childhood nickname, and Oliver had stubbornly refused to stop using it despite her protests.

Thea huffed impatiently. “What do you want?”

“This gala on Friday,” Oliver said, trying to keep his voice neutral, “is Mom making you go, too?”

Thea narrowed her eyes a little. “Yeah, why?”

The question brought him up short. He’d never been very good at coming up with convincing excuses. “Um.”

Her eyes widened, then, an expression of disbelief – and was that anger? disappointment? - on her face.

“Ollie, you cannot bail on this party. Don’t leave me hanging with Mom and her snobby rich friends just so you can get laid and drink tequila shots,” Thea complained, her tone a mixture of frustration and annoyance. “I won’t cover for you if you do, and Mom will only give you yet another lecture about responsibility and your duty to this family if you don’t go.” She said the last part with an exaggerated flourish, and more than a hint of sarcasm, which Oliver ignored, but he couldn’t help agree with her sentiment. Their Mom _would_ be pissed if he didn’t show up.

He just really, really didn’t want to go.

Eventually, Thea sighed in an overly dramatic fashion and said, “Okay, fine. If you want to leave early, I’ll cover for you. But that is _all_ , Ollie, I mean it. You might be my brother, but I’m not going to be your excuse every time you don’t want to do something.”

Oliver gave his sister a grateful smile. “Thanks, Speedy.”

“Don’t push it. I can still rat you out to Mom before Friday and you’ll get the lecture anyway.”


	5. Chapter 5

**Summary for the Chapter:**

> AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.
> 
> Written for the Olicity Fic Bang 2015.

**Notes for the Chapter:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning.
> 
> [Listen to _How To Be A Heartbreaker_ : The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

* * *

**Playlist for this chapter:**

1.  _Circus_ \- Britney Spears

2.  _Poker Face_ \- Lady GaGa

3.  _I Saw Her Standing There_ \- The Beatles

* * *

 

It was day seventeen.

The day of the Queen Consolidated monthly charity gala, where she would be expected to make her first move on Oliver Queen.

Her friends were counting on her to pull this off.

She was counting on _herself_ to pull this off.

The Moment of Truth had arrived at last.

 ***

Getting home from work that afternoon had been a struggle.

 It hadn’t been just because of the sheer amount of traffic passing through the centre of Starling City at rush-hour on a Friday, but because the thought of each minute that ticked by bringing her closer and closer to that evening’s events was starting to make Felicity’s heart beat fast and her nerves jangle. Her grip was unnaturally tight as she steered through the mass of cars and taxis and pedestrians, her watchful eyes fearful of the clock on her dashboard that ticked past 5pm just as she finally made it onto her street, counting down the minutes and the hours ‘til showtime.

Weird word, that, _showtime_. It was something her Mom would always say whenever she left for work, kissing the top of Felicity’s head in a flourish of hairspray and flowery perfume as she tottered out the door in her high heels, a feather boa wrapped around her shoulders or a dozen bracelets clinking on each wrist, her voice loud in their small apartment; “It’s showtime!”

Of course, her Mom was a cocktail waitress in Vegas, so perhaps the phrase was a little more apt for her.

 But this? This wasn’t so much entertainment as a mission.

 If she thought of it that way, there was less of a chance she’d lose it just hours before she had to be at the Queen mansion, dressed to kill with her game-face on and all the dignity she was able to muster.

First, though, she had to eat, and as she pulled into the parking lot of her building she mentally rifled through the various take-out menus she had in the drawer under the sink. By the time she reached her apartment, she was debating between Thai food and the old faithful Big Belly Burger, both making her stomach rumble at the thought of rich, greasy food that would give her that little bit of extra courage for what the night had in store.

Then again, maybe it wasn’t such a good idea to be eating a lot of junk food if she was going to be wearing a figure-hugging dress later.

So no Big Belly Burger, then. Thai food. That was healthier, right?

Felicity kicked off her shoes and shrugged her coat from her shoulders, crossing over to the small kitchen for the menu for the Thai takeout place she loved. Within ten minutes, she had ordered her food and was pulling her hair out of its ponytail to loosen it, feeling the ache at her scalp throb from having her hair pulled back all day.

As she waited for her takeout to arrive, she went into her bedroom to check on the beautiful blue dress she had picked out for that night. It hung off the door of her closet, sealed in a garment bag, having been carefully dry-cleaned and steamed that morning. She had left it at the dry-cleaner on her way to work, tipping the owner generously and paying a fair bit extra to have it ready as soon as possible, which she would undoubtedly regret next month, when the charge came off her only and rarely-used credit card. Laurel had picked it up during her lunchbreak and dropped it off at the apartment for her.

She regarded it now with an unusual scrutiny. Well, unusual for her. She had never been a “girly girl”; while she enjoyed clothes and make-up and liked looking nice, and always appreciated an opportunity to dress up, she had never been the kind of woman who insisted on looking like a catwalk model wherever she went. It wasn’t her kind of thing. She didn’t feel the need to look like she was dressed for the runway every time she left the apartment, and she had held fast to that philosophy.

And it wasn’t just because her love life had been on the slow side and therefore had no man to dress _for_ , thank you very much.

She simply believed that her value lay in what was inside her head, not what was on her body.

Unfortunately for Felicity, that way of thinking wasn’t what was going to get her noticed if she planned on trapping someone like Oliver Queen in her sights. He was a famously shallow playboy, with little interest in anything but the physical attractiveness of a woman in question and the level of alcohol in her blood.

The dress, sapphire blue and made of shimmering silk that fell to her ankles, was guaranteed to catch his eye. It would be the flame to his moth, drawing him to her.

After that, she just had to watch what she said and make sure she didn’t try to bite off her tongue again.

When her food arrived some twenty minutes later, she wasted no time in devouring it, storing up her energy as she ate her stir-fried beef and vegetables straight out of the carton. She dumped the empty box in the trash when she was done, then headed straight for the bathroom, where she set the shower running on the hottest temperature she could bear so that the small room filled with steam, fogging her vision and her mind and stopping her from overthinking.

_Relax_ , a voice that sounded a lot like Sara told her from the back of her mind. _You may be on a mission, but you can still have fun tonight. Drink. Mingle. Enjoy yourself. This is a prestigious party; you’re an honoured guest. A QC employee. You have a right to be there._

When she could no longer see in front of her own nose, never mind anything else, Felicity stripped off her office attire and glasses and jumped under the hot spray, relishing the heat and pulse of the water to keep her nerves calm. She washed quickly but methodically, inspecting her legs and underarms for stray hairs that were not welcome and was pleased when she found none; her hair, she paid particular attention to, washing it twice with her favourite (and very expensive) rose-scented shampoo, making sure it was squeaky clean. When she was satisfied, she turned off the water and wrapped herself in a lilac towel, letting her hair drip onto the floor as she padded back into the bedroom.

The blue dress stared at her from its garment bag, teasing her.

She crossed over to her nightstand to check the time. Her alarm clock read 5:45pm. Two hours and fifteen minutes till she had to be ready to present herself to Starling City’s richest of the rich. It felt like a very long time and not enough time, simultaneously.

She dried herself off, wringing out her wet hair, and changed into an old t-shirt and loose maroon yoga pants before attacking her make-up drawer, arranging her products on the small vanity opposite her bed. She was amazed at how much she actually _needed_. Did it always look like this much? Perhaps she’d never noticed.

Felicity dug through the drawer before coming up with a bottle of nail polish the same colour as her dress. Her nails were aquamarine at the moment, but the colour was chipping, and she’d been meaning to replace it with a different shade…

She put the bottle on her vanity, next to the mascara and a tube of pearly pink lipstick.

Next, she started on her hair. It was already starting to frizz as it dried, a blonde cloud around her face, and in the mirror over the vanity table, she looked like a dandelion clock, albeit more pink-faced. _No_. It would have to be tamed into submission. She grabbed her hairdryer and a hot pink curling iron – a gift from her mother two birthdays ago – and then her phone buzzed.

Felicity crossed to the other side of the room to check it, and saw that she’d had a text from Sara.

**From: Sara Lance (5:47pm)**

_Feeling nervous?_

Felicity smiled to herself. She could always trust Sara to look out for her – and to know when she needed some reassurance. She quickly typed a reply.

**From: Felicity Smoak (5:48pm)**

_A little_.

**From: Sara Lance (5:51pm)**

_Want me to come over?_

She considered this for a moment. Some company might help to distract her from how nervous she still felt. And Sara understood her better than almost anyone.

Plus, she could paint her nails for her, if she asked her nicely enough. Or bribed her with the chocolate dessert she still had in the fridge.

**From: Felicity Smoak (5:53pm)**

_Yes, please!_

Her phone buzzed for the third time.

**From: Sara Lance (5:54pm)**

_Be there in 10. Will bring mood relaxers :)_

That was “Sara code” for alcohol.

Somehow, she didn’t mind the extra courage. Even if it was the liquid kind.

Ten minutes later, Felicity had successfully dried – though not so much tamed – one side of her hair when there was a knock on the door and Sara came in, the distinct clank and rattle of glass bottles reaching Felicity’s ears as she made her way through the apartment to where Felicity was, a bright smile on her face. Her face was bare of make-up and her skin that that prettily flushed look that Felicity had always envied; she must have come straight from her thrice-weekly training sessions at the gym, because she was wearing dark yoga pants and a pale grey tank top, but she didn’t look it. Twenty minutes with her Pilates DVD and Felicity looked like a tomato. Sara just looked the way she always did, fit and toned and healthy and not an inch of ghastly redness in sight.

It sometimes made Felicity hate her.

“Hey, gorgeous,” Sara said by way of greeting, plopping herself down on the end of Felicity’s bed and shrugging out of the baby-pink hoodie she wore over her workout clothes. She patted the bag at her feet. “Gifts for the nervous lady. It’s cheap, but it’ll take the edge off.” She grinned toothily.

_Good_ , Felicity thought. _I need to not think too much tonight_.

She picked up her hairdryer, then put it down again. “Do you really think I’m dating material?” she asked suddenly.

Sara peered at her curiously, still smiling her toothy smile, then jerked her head in the direction of her closet. “In that dress? Absolutely.”

“I’m serious, Sara,” Felicity implored, pushing a hand through the one side of her hair that was still damp. “I need to know. Would _you_ date me?”

“Only if you’d let me bring you to the gym in my building three times a week with no complaining.”

“ _Sara_.” She wasn’t taking this seriously. And as much as Felicity usually loved Sara’s teasing and semi-flirtatious banter – having a female friend who liked women did wonders for your self-esteem – she kind of needed her to give a serious answer right now.

“Okay, okay,” she conceded. She got up from her perch at the end of the bed and crossed over to where Felicity sat at her vanity, crouching down to her shoulder level (which wasn’t difficult since Sara was pretty short) and giving her best _serious face_. “I’ll give you three reasons why you’re dating material. One, you’re gorgeous. Two, you’re crazy smart. And three, you don’t pretend to be anything but who you are. If any guy doesn’t see you as girlfriend material, the problem is with them, not you. You just have to show them that it’s their loss.”

Sara was right. Felicity knew that she was. She was an MIT graduate, dammit! And she worked for one of the biggest, wealthiest, and most influential companies in the area. She was a _catch_.

Sara stretched to her full height again, placing both hands on Felicity’s shoulders. “C’mon. I’ll do your hair for you, a little parting gift before we ship you off to Starling high society. And don’t give me that look,” she added, when Felicity looked at her with a decent amount of scepticism and disbelief, “I trained as a hairdresser when I dropped out of college. I know what I’m doing. Let’s give Oliver a reason to look twice,” she gave her a wink, “and regret it if he doesn’t.”

It was a tempting offer. And with the nerves bubbling in her stomach, she didn’t entirely trust herself not to set her hair on fire while handling a curling iron. She doubted that the Queens would appreciate the singed-hair look. So maybe entrusting her hairstyle to Sara’s care was the best option.

“Okay,” Felicity agreed, “but can we have some of that wine first?”

 ***

The vast ballroom that Oliver remembered from parties and high society functions as a kid, but had seldom entered since then, had been transformed into a lively buzz of chatter and the rise and fall of violin music when he finally arrived downstairs at 8:05pm, a wall of noise greeting him as he reached the hallway and cringed inwardly at the sight of so many people filling the large space. The cavernous ceiling, with its gold-leaf three-dimensional design, only amplified the sound of laughter and talking, and the swell of the music.  

A nightclub, with its near-total darkness and tightly-packed bodies and pounding beat, he could handle. A party like this, with an orchestra and champagne and small talk with people who expected him to follow in his father’s footsteps, was less of an ideal Friday night and more of a personal nightmare.

_Why_ had he been roped into this, again?

“Oliver, there you are!”

He turned as he heard his Mom call his name, breaking away from a small group of people near the doors, which had been thrown open as an invitation for all to join the festivities, to head in his direction. She was already holding a glass of champagne, and her free hand rested on his arm just above his elbow as she leaned into him and murmured, “You’re late.”

“By five minutes, Mom,” he replied tightly, already starting to feel uncomfortable. And he hadn’t even entered the room yet.

“You’re still late,” she said, undeterred. Oliver decided it was no use fighting her on the matter. Moira Queen was nothing if not persistent. “Come, we have guests. It’s best we don’t keep them waiting.”

Oliver allowed himself to be steered into the room, plastering on as genuine a smile he could muster as his mother stopped to introduce him to her friends or speak to the many important people who had gathered in their home to pledge their money to a good cause. He recognized only a few of them, and mostly by their faces and not their names; people he’d seen coming to and from his father’s office at Queen Consolidated, or attending various business lunches his parents held for the Board and the top-ranking employees. None of them stood out to him as being particularly memorable.

As he finally managed to break away from his mother and moved further into the room, the air became thick and close with the warmth of too many people in one space, and he gratefully accepted a chilled glass of champagne from a passing waiter. He’d promised his Mom he’d “mingle” with the guests, but he didn’t particularly want to talk to any of them for any length of time, not if they were just going to compare him to his father and ask him when he planned on taking over the company.

The answer to that question, if he had his way, was _never_.

He silently cursed whatever business had meant that his father hadn’t been able to show up tonight. He could fake a smile and put on the charm, but he could never muster the sincerity and genuine warmth his father had when entertaining guests or trying to pull a crowd. As much as these monthly galas were for show – a chance to flaunt the wealth and success of the family – his father had always cared about the causes they supported. He had compassion and empathy. He just as easily gave back to the city what he took from it in company profit.

Oliver had never been like that. He somehow doubted he ever would be. Then again, maybe he just wasn’t trying hard enough.

He sipped his champagne, content to observe the room from a distance for the time being, and didn’t realize that Thea was at his elbow until her voice piped up over a climax in the music.

“You having fun?”

Oliver noticed that she was holding her own glass of champagne. Didn’t the waiters know she wasn’t old enough to drink? Or had she simply stolen it from a passing tray and nobody had noticed?

“Is that a serious question?” he replied, his gaze flicking from guest to guest as he twirled his now empty glass absently in his hand. At the far end of the room, he could just about see Walter Steele, the VP of Queen Consolidated and a close friend of his father’s, talking to a woman he thought he recognized from the Applied Sciences Division of the company. “You know I hate these things.”

“It might be a little more fun if you drink more,” Thea said conspiratorially, indicating her champagne.

Oliver frowned. “Thea…”

She rolled her eyes at him. “Relax, I’m kidding! Jeez, you and Mom are so uptight.”

_I wouldn’t have to be if you didn’t insist on being so reckless_ , is what comes to the forefront of his mind, but he bites his tongue and swallows down the retort because they’re at a nice party with important people and he doesn’t want to get into an argument with her right now.

Instead, he said, smiling at her, “You should go talk to people. Find Mom. Let her show you off.”

Thea pulled a face, but relented. “Fine. I’ll go be a ‘daughter of society’, or whatever. But I get to keep this,” she lifted her champagne glass.

“Just don’t let Mom see you drink it,” Oliver cautioned, and Thea nodded as if to say _Do you think I’m that stupid?_ before turning away from him and walking back into the crowd.

If he couldn’t keep Thea under control, it was going to be a long night. He was suddenly very jealous of the fact that Tommy was an only child.

He also needed more champagne, and went in pursuit of a waiter carrying a full tray back from the open bar at one end of the room, without noticing that somebody else was also heading in the same direction.

A somebody who collided with him rather painfully when they both reached the waiter at the same time, causing the tray to be knocked from the waiter’s hand and a dozen fine glasses of champagne sent crashing to the highly-polished floor, soaking their shoes and the hem of the person’s – the woman’s - dress with a small but rapidly-spreading lake of pale yellow champagne.

Because it _was_ a woman. A woman in a blue dress made of shimmering silk with a low, low neckline that was accentuated by long curls of blonde hair brought over one shoulder, and a red-lipped mouth that was currently open in a rather comical _O_.

And the first thing she said once she appeared to have gotten over her shock was, “Oh, _frack._ ”

 ***

“Oh, _frack_ ,” Felicity cursed, standing like a deer in headlights in the middle of the puddle of champagne she had sent crashing to the floor when she’d collided with Oliver Queen. _The_ Oliver Queen. The man she was supposed to be here to _impress_ , not….well, literally anything else.

As if almost biting off a good portion of her tongue the first time they’d spoken wasn’t enough of an embarrassment, she’d had to go ahead and smash about a dozen glasses of probably very expensive champagne in the middle of a crowd of people because she wasn’t watching where she was going.

And she was still standing in the puddle.

“Mr. Queen-“, the waiter started to protest, but Oliver held up his hand to stop him. She had thought he would be angry, but he didn’t seem to be. In fact, he was actually smiling, and at this distance, she could see the dimple in his right cheek that made him look almost boyish - and very, very cute.

“It was just an accident,” he explained. “I wasn’t looking where I was going.”

_Wait, what?_

She opened her mouth to protest, to say that the fault was all hers, but Oliver was still smiling that damn smile, with that damn dimple in his cheek that made her knees go slightly weak where she stood.

“Do you need some help?”

He directed his question to her, but she barely heard him, too busy was she taking in the look of him in a sharply-pressed black tuxedo and _this close_ , close enough to get a whiff of his cologne (over the rising aroma of spilled champagne) and to appreciate the broadness of his chest and shoulders in the jacket of the suit.

“Uh, miss?” the waiter said, somewhat nervously. “He’s talking to you.”

“What?” Felicity started, then gasped as she realized she’d been ignoring him the whole time. “Oh! Oh, I’m sorry. Uh, yes. I would like some help. There’s – glass, and – I’m all wet. Well, _I’m_ not, I mean, my dress is. The bottom of the dress. Is wet. Because of the champagne. Obviously.”

_Ground, please open up and swallow me whole._

Much to her surprise – and a sudden racing of her blood that had nothing to do with the heat of the room, nor the blush she was sure was spreading across her collarbone and exposed chest – Oliver touched a hand to her bare elbow as he gently steered her away from the sticky mess of champagne and broken glass, a gesture she found to be quite sweet as they moved from the close-packed crowd toward the main doors of the ballroom, where it was cooler and the air less dense from the heat of so many bodies.

Half of her brain was screaming, _oh my God!_

The other half was logical, reasonable, in its firm reminder that she wasn’t there to flirt for the sake of flirting. She was there to enact the plan to make him fall in love with her. And she had to keep her mind focused on that task, and not on the way his hand moved from her elbow to the small of her back, keeping her steady while his skin blazed hot through the material of her dress and she tried not to think of how close his hand was to her ass.

Nope. Not thinking about that. Not at all.

“Better?” he asked her, and this time she was determined not to space out on him.

“Yes. Thanks,” she replied. “For rescuing me. And for not, y’know, getting mad at me for being such a disaster area. I swear I’m more competent than this usually.”

Oliver laughed, warm and not at all condescending or derisive, the way he _could_ have done. It was a nice sound. “Oh, I know. You’re the woman who knows how elevators work because you went to MIT, right?” There was a twinkle in his eyes that said, _Got you this time._ It made her insides melt a little.

“Yep, that’s me,” Felicity said. “I, uh, hope I wasn’t totally embarrassing when I said that. Um. I wasn’t trying to be, I just – sometimes things don’t work out in my head the way I want them to and it does not, um, go well.”

_Stop babbling!_

“You weren’t,” he replied, and he seemed to mean it. He shoved his hands into the pockets of his pants, and she almost immediately missed the way his palm had felt against her spine.

_Focus on the plan, Felicity. Do_ not _get sidetracked._

“Oh! I should probably introduce myself, right? Since you rescued me from the spilled champagne and all,” she said. “I’m Felicity. Felicity Smoak. I work in the, uh, IT department. At Queen Consolidated. Which you already knew, of course, because you saw me there. In the elevator.”

Oliver stuck out his hand. “Oliver Queen. Though I’m guessing you already knew that, too.”

“Yes,” Felicity said, a little breathless. “I know who you are.” She took his hand and shook it, partly because he was obviously expecting her to and partly because she wanted to know how it would feel. And _wow_ , he had nice hands. “Should I call you Mr. Queen, or – do you prefer Oliver?”

_Focus._

“Oliver, please. Mr. Queen is my dad, and I would…rather not be addressed so formally as to be reminded of him.”

_Interesting._ She wondered why he had such an objection to being associated with his father. There must be some kind of story there.

“Oliver,” Felicity confirmed, and it sounded nice to say it. It was a nice name. She liked his name.

She liked _him._

And….she was still holding his hand. Or he was holding hers. Either way, they were still touching, and Felicity was beginning to feel kind of sticky in her shoes where the champagne had spilled on them, and she would probably need to take her dress to the dry-cleaners (again) to get rid of the alcohol stains, and….

He was staring right at her.

Oh.

“I should probably….go,” Felicity said. “My toes are kind of sticky, and the dress will need to be cleaned, and I’m still holding your hand so I’m going to let go of _that_ ,” – she did so – “and, uh. Hopefully I haven’t entirely ruined your evening?” She gave a nervous chuckle.

“To the contrary,” Oliver replied softly. “I think that coming tonight was the best decision I could have made.”

“Even though I spilled champagne everywhere and broke about a dozen fancy glasses and almost knocked you over?”

“Yes,” he said, firmly, and she believed. Believed him. “It was better than listening to boring rich people talk about how much money they have all night and being a show dog for my Mom.”

“You say that like you’re not one of them. The boring rich people,” Felicity clarified, when a moment of confusion passed over Oliver’s face.

“I can assure you, Felicity, that I get called many things, but boring isn’t one of them,” he said, almost conspiratorially, like he was letting her in on a secret. She got another whiff of that rich cologne, and she longed to stand closer and just breathe it in, but she couldn’t. Because she had a plan. She had a mission.

She couldn’t compromise it now just because she was very, very…. _attracted_ to him. Physically.

And she really did have to leave.

“If you insist on leaving, let me at least buy you a drink. On the house.”

Felicity frowned a little. “Isn’t it an open bar?”

For the third time that night, Oliver laughed, and for the third time, she didn’t feel like he was laughing _at_ her. No, he was laughing _with_ her.

“Yes, it is,” he affirmed. “But I’d still like to have a drink with you.”

_Play it cool,_ a voice that sounded a lot like Laurel told her. _You need to make him go after you. Leave him wanting more._

“I’m gonna have to say rain-check,” she said, “mostly because my feet are starting to stick to my shoes, but also because I work at your father’s company, and that would make things awkward, don’t you think?”

She cocked her head to the side, waiting for Oliver’s reaction.

“It doesn’t have to be awkward if you don’t want it to be,” Oliver persisted. “What my dad doesn’t know won’t hurt him. And since he’s not here tonight….”

_….he never has to know_ , she finished for him, in her mind.

But Felicity wasn’t here just to fall at the first metaphorical hurdle.

“We’ll see,” she said, looking up at him through her eyelashes, taking in the way his Adam’s apple bobbed slightly as he swallowed.

“I know where you work, you know,” he added. “I can always find you and keep asking you for that drink.”

“I guess you’ll have to keep asking, then,” was all she gave in reply, before she turned and walked away, careful to sway her hips a little as she crossed the red-carpeted main foyer and disappeared out of sight.


	6. Chapter 6

**Summary for the Chapter:**

> AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.
> 
> Written for the Olicity Fic Bang 2015

**Notes for the Chapter:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning.
> 
> [Listen to _How To Be A Heartbreaker:_ The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

* * *

**Playlist for this chapter:**

1.  _Ways To Go_ \- Grouplove

2.  _Call Me Maybe_ \- Carly Rae Jepsen

* * *

 It was 2AM by the time Felicity finished her first entry for the website, devoid of her champagne-stained dress and sticky shoes and dressed in comfy lavender sweatpants and a tank top. Her hair had been shaken loose of the pins holding it in place and was pulled back in a ponytail, away from her face, as she concentrated on getting down all the details that were important in relating the evening’s events.

Then again, it hadn’t been hard to recall the exact blue of Oliver’s eyes, or the way he’d laughed instead of getting angry that she’d spilled his family’s very expensive champagne, or the feel of his fingers on the small of her back as he’d guided her from the ballroom and the mess of glass and alcohol she’d left behind.

Remembering all of those details…was easy.

It also made doing her job, observing from a distance, looking at the facts and recording them, _faking the entire thing_ , a lot harder.

She nursed a cup of hot cocoa as she typed the last few words and pressed _Save to Drafts_ , satisfied that her account of _Day 17 – First Contact_ would live up to the standards of her friends.

Squinting at the hot-pink background of the blog, Felicity put down her almost-empty mug and rubbed at her tired eyes.  At least she’d been able to get the ball rolling without making _too_ much of a disaster of things, broken glasses and spilled champagne aside.

And she had a promise from Oliver that he would keep asking her out until she said yes. That was her treasure, her key.

By her own quick mental calculations, she figured she’d give him three or four days, but no more, before giving him her answer. It would be long enough to make him wait, to possibly wonder if she would accept him at all, before giving in to what he clearly wanted. She was on a deadline, and things needed to move fast – but not so fast that he got wind of a potential scam and called it off, finding someone new to pursue.

At 2:10AM, Felicity finally put her laptop aside and resigned herself to her bed, unable to keep her eyes open any longer.

Just forty-two more days to go.

 ***

True to his word, on Monday morning, Felicity was greeted by the presence of Oliver at her desk when she returned from her regular 10:30am coffee run to the vending machine in the IT Department’s break room.

To see him standing there, arms crossed, leaning against the edge of her cubicle with an expectant smile on his face, gave Felicity a great sense of satisfaction, as well as a sense of accomplishment.

So it had worked. The teasing and the flirting.

Huh.

“What can I do for you, Mr. Queen?” Felicity kept her voice even, nonchalant, as she sat down at her desk and took a sip of her coffee. She flipped through some papers, typed a few words on her keyboard.

All while pretending she had no idea why he was there.

“Have a drink with me.”

Felicity paused, mid-word, letting her fingers hover for a moment over the keyboard.

She had to hand it to him. It was honest, blunt, and straight to the point. Pretty bold, considering that they’d only just met “officially” a couple of days ago.

So _this_ was how Oliver Queen hit on women.

She couldn’t say she was particularly impressed.

“I think you’re forgetting the magic word,” Felicity quipped, taking a gulp of her coffee with an eyebrow raised in his direction.

Oliver uncrossed his arms and came around the edge of the cubicle, so that he was standing almost right behind her. His presence was very _large_ , filling the small space, and she was very aware of his broad chest just inches from her face. “And what word would that be, Miss Smoak?”

“Nuh-uh,” Felicity shook her head, pressing her lips together. “If you don’t know the answer to that, I’m not going to tell you. Figure it out yourself. You’re an adult.” She peered at him. “You _are_ an adult, right?”

Oliver huffed out a laugh, the dimple returning to his right cheek. “Yes. Yes, I am.”

“Then you should be able to figure out what the magic word is, shouldn’t you?” Felicity said with a smile and, with rather more flair than she was used to – and since when did she have _flair_? – turned back to her computer and picked up her work where she had left it ten minutes ago. She concentrated hard on hitting the right keys and definitely did _not_ think about the expression that might currently be on Oliver’s face. The expression she couldn’t see, because she rather pointedly was _not_ looking at him.

Still, he didn’t immediately leave, or say anything in reply.

Time to hammer home the point.

“When you inevitably come by and ask me out again tomorrow, I want to hear that magic word, or I will just keep saying no until you do,” she told him, trying to sound as bored by this prospect as she possibly could, “ _Oliver_.”

“Are you offering me a challenge?” he replied, amused, but otherwise showing no signs of being bothered by her words.

“I guess I am,” Felicity shrugged, reaching for her coffee and letting her fingers tap an absent rhythm on the rim of her mug. She knew he would notice the dark, midnight blue colour that she had painted them. It was the same colour she had been wearing at the gala. “Is that something you’re interested in?”

For a moment, Oliver’s eyes narrowed, as if he couldn’t quite figure her out. A crinkle of confusion appeared between his eyebrows. What kind of game was she playing? Felicity thought she could _see_ the question turning in his head, trying to match the nervous, babbling girl from the elevator and the sophisticated-but-clumsy guest at the gala to the woman in front of him, who had now rejected him for a second time on the grounds that he hadn’t said “please”.

(That was the magic word she was going for. _Please_. If she was going to fake-date Oliver Queen, she was going to make him learn better manners than the ones he exhibited in the tabloid pages.)

“I’m interested,” he finally declared.

“Good,” Felicity said. “That makes one of us, then.”

She threw a bright smile over her shoulder, showing off her blonde hair and the sparkle of a tiny turquoise stud in her right ear.

It was worth it just to see the dumbfounded look on his face.

“I guess I’ll let you get back to work,” Oliver said, that small smile playing around his lips once more. “Have a nice day, Felicity.”

“You too,” she replied, “Oliver.”

But he was already out the door, leaving a faint whiff of cologne behind.

 ***

The following day, at 10:25AM, Oliver was back. And he wasn’t empty handed this time.

“Coffee,” he announced, setting the steaming to-go cup on Felicity’s desk.

Felicity was immediately drawn in by the delicious smell of dark-roast coffee beans – how did he know she liked dark roast? – but then stopped herself, pausing with her hand outstretched, fingers reaching for the cup in mid-air.

She pointed to the cup, narrowing her eyes suspiciously. “Did you poison this? Am I going to get roofied _at my desk_ , in the middle of the day, on a Tuesday? Is this your grand plan to ask me out? Because if it is, you are a _lot_ less classy than you make yourself out to be. And a pervert.”

“No roofies,” Oliver promised. “Just coffee. And I’m not a pervert.”

 _That’s exactly what a pervert would say,_ Felicity thought, though she didn’t say anything out loud. Instead, she took a sip of the coffee he had brought her.

Just to make sure he really hadn’t poisoned it.

“Oh my God,” Felicity groaned involuntarily, “this is the best coffee I’ve ever tasted.”

Oliver had the nerve to look smug. “I told you it wasn’t poisoned.”

“Seriously,” Felicity asked, “where did you _get_ this? The coffee in this building _sucks_.” Then, eyes flying wide, she realized what she’d said and backtracked quickly. “I mean, it’s – okay, I guess, as far as coffee goes. Not that your dad is responsible for the quality of the coffee. Or, I don’t know – is he? Is coffee quality control part of being a CEO? Is that a thing?”

“Next time I see him, I’ll ask,” Oliver chuckled. “But this particular coffee is not from this building…and if you agree to go on a date with me, I’ll tell you where I bought it.”

_Wait._

Felicity put down the cup. “You bribed me.”

At that, Oliver looked hopeful as well as smug. “Did it work?”

She thought about this. “No.”

When he appeared to want an explanation, she continued, “You didn’t use the magic word. So getting me the most delicious coffee in Starling City – and it _is_ the most delicious coffee in Starling City, it’s the most delicious coffee I’ve ever tasted -  is not going to work.”

 _Either he’s a lot more stubborn than he looks, or he’s a lot less smart than he wants people to think he is_ , she thought. Oliver was fast becoming a whole box of contradictions. Gentlemanly and flirtatious, yes, but also a little crass, and most certainly entitled.

Maybe this would be a little harder than she thought. Playing hard-to-get with someone who clearly had a one-track mind and very little experience of deviating from tried-and-tested methods might not be the best option.

“Try again tomorrow,” Felicity said, picking up the coffee again and sipping at it – it was hot, but not scalding, and just sweet enough that it would keep her energy sustained for another few hours – “Maybe the third time will be the charm. And yes, I will need more of this delicious mysterious coffee.”

And just like that – just like the previous day – he was gone, without so much as a word of a reply.

 ***

Wednesday morning greeted her with the sound of her alarm blaring at 7:15am instead of 6:10am, like it was always supposed to, and a loud string of curses fell from her lips as she realized that, for the second time in the three weeks since she had started working at Queen Consolidated, she was going to be late for work.

_Frack._

She dressed and brushed her teeth hurriedly, pulling her hair back into its usual work-appropriate ponytail and shoving her feet into her shoes just minutes before she threw herself into her car and stamped on the gas pedal, going as fast as the speed limit in Starling City would take her.

When she reached the lobby of Queen Consolidated, the receptionist – Peggy – told her not unkindly, “You’re late, Miss Smoak,” as she rushed past towards the elevators and pressed the button for the IT Department’s floor.

 _I don’t need to be told I’m late, thank you very much_ , she thought, _I’m already freaking about it enough, without the reminder._

Dashing to her desk while simultaneously pulling off her coat, Felicity was in her seat and logged on to her workstation computer before she noticed that anything was amiss.

Or rather, it wasn’t what was missing. It was what was _new_.

Like the tall, steaming cup of coffee and what looked like a pumpkin spice muffin in a small white paper bag that definitely _wasn’t_ something that was likely to be on her desk.

She did love pumpkin spice muffins. She loved pumpkin spice anything, really.

But how did he _know?_

Because of course this was Oliver’s doing. How could it _not_ be?

She pulled the muffin from its bag, taking a large bite out of it as she pulled up that day’s work on her computer. She had a few emails to answer first, and then some databases to update. Easy stuff, simple, straightforward. For her, at least.

It should give her ample time to figure out her next plan of attack.

And the muffin was delicious.

Felicity reached for the cup of coffee, longing to taste the rich dark-roast beans again – the _smell_ alone was intoxicating – but stopped when she noticed something written on the side of it.

Turning the cup around, she saw one word – a question – and a string of numbers below it, written in what could only be Oliver’s own handwriting.

_PLEASE?_

Underneath was his cellphone number, curling around the side of the cup with a smiley face drawn on at the end.

Felicity bit back a smile. So he’d listened, and done as she’d asked. Impressive. She had to admit, it was pretty cute. And kind of romantic. Oliver struck her as the type of man who was more likely to slip his number not-so-subtly into the cleavage of whoever he’d chosen for the night, not write it on the side of a coffee cup and deliver it anonymously along with baked goods.

She wasn’t going to complain, though.  She already had what she needed.

Pulling out her phone, she took a quick photo of the coffee cup, careful to make sure that the actually-kind-of-sweet smiley face doodle was in the frame. It would make excellent evidence when she wrote about this for the blog. She then carefully put Oliver’s number into it, checking it twice to make sure she got the digits all correct.

And after that, she devoured the coffee and the rest of the muffin as if her life depended on it.  Food and drink _that_ good should never go to waste.


	7. Chapter 7

**Summary for the Chapter:**

> AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.
> 
> Written for the Olicity Fic Bang 2015.

**Notes for the Chapter:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning.
> 
> [Listen to _How To Be A Heartbreaker:_ The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

* * *

  **Playlist for this chapter:**

1.  _Little Numbers_ \- BOY

2.  _Something In The Way You Move_ \- Ellie Goulding

3.  _Free_ \- Ryn Weaver

* * *

 Felicity turned her phone over and over in her hands, her stomach writhing with nerves. She’d been staring at it for the better part of an hour, all through dinner and now while watching TV, trying to figure out what to say when she eventually made use of the fact that she was now in possession of Oliver’s cellphone number.

Eventually.

As of yet, she couldn’t think of anything appropriate to say. She doubted that a mere _thanks for the coffee_ would suffice. Even though it had been pretty damn good coffee.

Felicity knew that Oliver would be expecting more. He’d given her his number for a reason. She’d just never had any experience with this sort of thing. Especially in the context of faking a relationship and a romantic interest that simply did not exist.

It was at times like these that she’d wished she’d been more romantically active in college. She’d had a couple of boyfriends, sure, and then there had been Ray in her final year of her Masters’, but casual dating and all that that entailed had mostly passed her by.

She was disappointed in her past self.

She could have used her past self’s experience in the matters.

As it was, she was saved from thinking about it too much by the sound of her phone ringing. It was Laurel; just the person who might be able to help her.

“So, a little birdie told me that you got our subject’s number today,” Laurel said, by way of greeting, once Felicity answered the call.

“Sometimes I really wish I hadn’t befriended two sisters,” Felicity muttered, mostly to herself, but also for Laurel’s sake. “You talk to each other too much. And yes, I did, though I told Sara not to tell you that.”

“Well, she didn’t tell me _everything_ ,” Laurel clarified. “Just that he left you his cellphone number at work when you weren’t at your desk. That’s what happened, right?”

“Yes…and no,” Felicity said, drawing her knees up to her chin where she sat on the couch, recalling the events of the last few days and what had happened that morning. “He got me a muffin, Laurel. _Pumpkin spice_. You _know_ how much I love pumpkin spice. And he got me coffee. Not crappy coffee, either. This was real, honest-to-God, ‘the best coffee you’ve ever tasted’ coffee. And you know how I feel about good coffee.”

Laurel listened to all of this in silence, letting Felicity fill her in on what had happened without any input from herself. She got the impression that she was weighing what Felicity was saying very carefully in her mind, exactly like the lawyer that she was.

Eventually, she replied, “I’m impressed. He’s actually making an effort. Not what I expected from Oliver Queen, notorious playboy and spoiled brat, but you know what they say; people can surprise you.” She paused, sounding a lot less like a lawyer and more like Laurel, one of her oldest and closest friends who was just as giddy about the situation as she was, as she added, “Nice work, Smoak.”

Felicity couldn’t help herself; she grinned.  “I know, right? I didn’t expect the whole playing-hard-to-get thing to _actually_ work, mostly because Oliver has a _very_ one-track mind – I mean, really, talk about being completely unable to change to external circumstances -  and at first I didn’t think he’d take the bait, but it worked. And I got his number written on the side of a coffee cup, like we were in a movie or something. Who does that? Unless you’re Ryan Gosling in _The Notebook_.”

“He must like you,” Laurel said. “Which is good. It’s very good, in fact. This is what you want, remember? It’s what _we_ want.”

“I know, I know,” Felicity replied. “It’s all part of the plan to metaphorically leave him at the altar, because he’s gross and a douchebag who treats girls like they’re shiny toys.”

_He’s pretty hot though,_ her brain supplied, not entirely voluntarily. She pushed the unwelcome thought down. This wasn’t about physical attractiveness, or physical attract _ion_. This was about revenge, and making Oliver look like an idiot for thinking he could pull the whole charming-and-chronically-emotionally-unavailable schtick for the rest of his life, going through scores of women like Felicity (and most other people) went through toilet paper.

Which, okay, probably wasn’t the best metaphor to use, because _ew_. She really didn’t need to think about Oliver Queen and toilet paper in the same thought.

“Exactly,” Laurel confirmed, bringing Felicity out of her mini-reverie. “So, how long are you gonna wait to call him?”

Felicity wound a curl of hair round and round her finger distractedly, pressing her lips together as she thought about this. “That’s the thing. I don’t _know_. I was hoping you would have some better advice.”

“Your goal is to make him to come you, so you have to make him wait. I’d say….twenty-four hours,” Laurel suggested, “give or take. It’s pretty obvious he wants to ask you out, and it’s pretty obvious that he wants you to say yes. Guys don’t get coffee for girls they don’t want to say yes to a date.”

“Twenty-four hours,” Felicity mused, “so, that’s…tomorrow. Are you sure? Isn’t that a little too long to make somebody wait to accept a date? I have a deadline, remember.”

Laurel chuckled. “Felicity, darling, you’ve been out of the dating game for far too long. This kind of thing is normal, trust me. Twenty-hour four hours is just the right amount of time before you say yes. Don’t worry about the time-frame. You still have thirty-eight more days.”

She decided that it couldn’t really hurt to take Laurel at her word. She trusted her; this whole thing had been _her_ idea, after all.

“Twenty-four hours it is,” Felicity said, with finality.

“Keep me posted,” Laurel said, “and make sure you tell the others, too. They’ll be desperate to hear what you’re going to do next.”

“Oh, I’m sure,” Felicity replied, the barest hint of sarcasm in her tone. “Just make sure that none of you _actually_ come on the date with me and Oliver, okay? ‘Cause I really don’t know how I’d explain that to him. And, to be honest, it’d be a bit of a mood killer.”

Laurel laughed again. “I’ll let them know. No stalking allowed.”

“You better remember that,” Felicity warned. “I’m holding you to it.”

“I certainly will,” Laurel said. “But I have a ton of casework to do, so I’m leaving this in your capable hands for tonight. Bye, Felicity.”

“Bye.”

Felicity ended the call, feeling less nervous than she had been before, though still not completely satisfied that she knew what she was doing. Laurel was smart, and sensible; it would be unwise to ignore her advice. It was advice she sorely needed.

But at least she had a time-frame now. Twenty-four hours. That was doable. She could _totally_ wait twenty-four hours before accepting Oliver’s offer of a date.

Although, in his mind, it was probably less of an offer and more of a demand that he knew she would eventually acquiesce to, because he was Oliver Queen and she was, well, _female_ and single.

_Ugh_.

When she wasn’t in the immediacy of his (very, very) handsome presence, and distracted by his voice and his eyes and how very _tall_ he was, she remembered exactly how entitled he could be. As if she should make herself available to him purely because of her gender.

It was all the more reason why she was doing this…. _thing_ that she and her friends had cooked up. Girl power, and all of that.

And, the truth be told, it was fun to watch Oliver squirm.  She could only guess what his reaction might be when she eventually, finally, after three days of making him wait, agreed to go on a date with him.

 ***

**From: Tommy Merlyn (8:14pm)**

_Tomorrow night. You and me, a fancy restaurant just outside the Glades. What do you say?_

Laurel pursed her lips, squeezing her fingers around her phone as if she could _force_ the text message she’d received forty minutes ago to disappear. Ever since she’d made the mistake of giving Tommy her cellphone number just to get him to back off haranguing her whenever she showed up at his club, he’d texted and called almost non-stop. Apparently, he’d gone from harassing her in person to harassing her virtually.

The worst part was, she actually enjoyed it.

Tommy was the kind of man she avoided dating – at all costs. He was boisterous and flirty, and unapologetically so. He had money, and he had no qualms about where – or on what – he spent it. He was the type of guy who “didn’t do” girlfriends, preferring brief encounters and one-night-stands to a long-lasting, stable relationship. All the pleasure without the commitment.

He was, in fact, almost exactly like Oliver, who just so happened to be his best friend.  Which she knew because she’d done her research – on Oliver, on Tommy, on the social circles they moved in, the kinds of people that they were and the kinds of people they associated themselves with. The young, beautiful, idle rich. That alone should have been a glaring warning sign for Laurel; _do not approach, back off, dangerous. You will be hurt._

It was why, in the end, she’d chosen Oliver Queen as Felicity’s “subject” for the fake-dating-proposal dare.  Men like that deserved to taste their own medicine. 

But did that really matter when she was so undeniably attracted to one of those such men?

Laurel read the text message again. And again. And again.

_Could she say yes?_

_Did she want to?_

She’d told Felicity to wait twenty-four hours before accepting Oliver’s offer of a date. That it was customary to make a man wait, to show him that he wasn’t your only option, that you had other choices and while yes, you were interested, you weren’t above accepting another offer from another man at another time. To exercise _agency._

But right now, she didn’t particularly feel like taking her own advice. She really liked Tommy. And she knew that it would probably make her a bad friend if she went back on her own instructions to Felicity.

But the situations were different, she told herself. _Laurel_ wasn’t the one running an elaborate scam to seduce him into a fake relationship, get him to fall in love with her and propose, and then throw him out on his ass.

So, she was perfectly justified in accepting Tommy’s offer of dinner Friday night.

…..wasn’t she?

Without giving herself any time to talk herself out of it, she opened up a new message and quickly replied to Tommy’s earlier text.

**From: Laurel Lance (8:48pm)**

_It’s a date._

**From: Tommy Merlyn (8:49pm)**

_I knew you couldn’t resist me, Dinah Laurel Lance._

**From: Tommy Merlyn (8:51pm)**

_How does 8 work for you?_

Laurel bit her lip. She was actually doing this. She was actually _going on a date_ with Tommy Merlyn.

**From: Laurel Lance (8:53pm)**

_8 is perfect._

**From: Tommy Merlyn (8:54pm)**

_I’m already looking forward to it._

She only hoped this wouldn’t end badly – for either of them.

 ***

Felicity didn’t wait twenty-four hours.

She barely waited twelve.

She was far too nervous, far too keyed up about all the possibilities, and far too worried about wasting any of the precious time she still had left (thirty-eight days wasn’t _that_ much, after all, no matter how Laurel had made it sound like it was) to leave it any longer than another hour after she had spoken with Laurel. 

After pacing the small space that her living room offered for ten solid minutes, alternating between chewing at her nails and fidgeting with the end of her ponytail, frizzy from the day’s exertion, she decided that she was going to just….do it.

To hell with proper dating etiquette.

So maybe she jumped the gun a little when she pressed _Call_ at 10:15pm after a second bowl of ice cream and waited for Oliver to pick up, gnawing at the skin of her thumb in that agitated way she did when she was jumpy and nervous, chipping off some of her nail polish in the process.

Curled on the end of the couch, her phone pressed to her ear, she waited as the other end of the line rang and rang, until she started to wonder whether he would even answer – or if he’d given her a false number.

Then the line clicked on, and a familiar deep voice, slightly rough from the tiredness that came with the lateness of the hour, asked, “Hello?”

“Oliver!” Felicity’s own voice came out breathless from nerves; she dragged her fingers through the end of her ponytail distractedly, to try and regain some of her composure. “It’s – it’s Felicity. You know. From Queen Consolidated.” She paused, letting out an involuntary giggle; she felt like a fourteen-year-old schoolgirl, talking to a boy she liked for the very first time. “You gave me coffee with your number on it,” she added.

“Felicity!” Was it just her imagination, or did he sound more animated than he had been a minute ago? Like the rough edges of his voice had been smoothed out, just by hearing her name. But maybe, in her giddy nervousness and the novelty of the situation, she had made that up. She heard some shuffling on the other end of the line, and the squeak of what sounded like a chair – a desk chair? – and then Oliver cleared his throat audibly ( _so maybe he_ had _sounded overeager to hear from her_ ) and said, much slower and more deliberately, “Hi.”

Why, oh why, did he have to have a voice that made her toes curl with pleasure every time she heard it?

“Hi,” she said back. Then paused, giggling again, unable to stop herself. _Holy crap. She was talking to Oliver_ freaking _Queen on the phone._ She started fidgeting with the end of her ponytail again, just for something to do with her hands. “Um. Good evening? Is it normal for someone to say good evening when they call really late at night?”

“That depends,” Oliver replied, and she swore she could _hear_ the smile in his voice. “Are you having a good evening?”

_What was she supposed to say to that? Yes? No? Better now that I’m talking to you?_

Felicity cringed inwardly at that last option. There was flirting, and then there was outright cheesiness, and somehow she didn’t think they were “there” yet in terms of such sappy statements.

“Yes,” she affirmed, letting herself sink back into the couch, unfolding her legs from underneath her and stretching out her feet and toes. “Work is hell – not that your company, specifically, is hell, but you know what I mean. Or. I don’t know, do you? Because I get the impression that you don’t talk to many QC employees.”

“You don’t have to hide your feelings from me about working for my parents’ company, Felicity,” Oliver said, laughter in his voice. That surprised her. Then again, she remembered how he’d objected to being addressed as “Mr. Queen” at the gala, and she figured that he was being more sincere than he perhaps intended. “There’s a reason I don’t go there often, and it’s not just because of the terrible coffee.”

“Yeah, the coffee kinda sucks, doesn’t it?” Felicity agreed candidly, letting herself enjoy this moment. As if they were two people “in the know” sharing a private joke. Let him think that they had some kind of intimate understanding that only they were aware of; he’d given her a way in, and now she was forging a connection. It didn’t really matter whether one actually existed or not.

“Speaking of which….” Felicity wound a curl of hair round her finger, letting the words hang in the air for a moment before continuing, “you told me that if I agreed to go on a date with you, you would tell me where you bought that coffee you brought me.”

“I did, didn’t I?” Oliver said teasingly. “That is, if I’m right in saying that that was your way of accepting my offer of a date.”

There was no mistaking the hope in his voice this time. He _wanted_ her to say yes, to confirm his suspicions. To prove him right. To show that it had worked; that she’d succumbed to his charms.

“It was!” Felicity answered quickly, to give him no time to think too hard about his assumption. “I would very much like to go on this date you talk so much about. With you.”

“Somehow I get the impression that you just want to find out where I got that coffee,” Oliver joked.

“Maybe it’s both,” Felicity suggested. “Maybe I want the coffee _and_ a date with you. I’m a woman and a certified genius. I can multitask.”

“Can you multitask in, say…about ten minutes?”

“What? Why?” Felicity looked at the clock above the TV. It was 10:35pm. Had they really been talking for twenty minutes?

“It’s a surprise,” Oliver said cryptically. _Damn him._

“Oliver, please be serious. I have to work tomorrow,” she pleaded. What _was_ he doing? This hadn’t been part of her plan. This hadn’t been in the script she’d had in her head of how the conversation would go.

“Felicity, this _is_ me being serious,” he replied. “Can you be ready in ten minutes or not?”

“You’re not going to tell me why, are you?” she asked, the resignation clear in her voice.

“Nope,” he replied cheerfully.

_Oh, he was so irritating._

Felicity feigned a heavy sigh. “Okay. I can be ready in ten minutes. But you better not make me late for work tomorrow because I have to work at _your_ family’s company and if I get fired, let it be known that that _will_ be on your conscience.”

“I accept any and all blame for making you late for work tomorrow,” Oliver promised. “Is that better?”

Felicity acquiesced, though she kept her tone light and her words playful. “Do I really have a choice?”

Oliver chuckled. It was the kind of chuckle that sounded ominous, like he knew something she didn’t. An ‘I’m-not-telling-you-what-I’m-planning’ kind of chuckle.  It was infuriating. “Be ready in ten minutes. Text me your address.”

And then he hung up on her.

_The nerve of him!_

Her mind running wild, Felicity glanced at the clock over the TV again. 10:45pm. _10:45pm._ What could he possibly want to do at almost 11pm on a Wednesday night?

Jumping up off of the couch, she did as he’d asked and sent him a text including her address and directions to her apartment. Then she moved quickly throughout her apartment, brushing her teeth and re-tying her ponytail, before pulling on a thick, soft blue sweater and dark jeans over her pyjamas.

Her phone buzzed just as she was shoving her feet into the pair of bright red flats by the door, the ones she usually reserved for weekend grocery shopping or going to the drugstore for emergency tampons. She wasn’t really sure what kind of footwear one wore to an impromptu midnight (well, almost) mystery adventure with Oliver Queen.

So, red flats it was.

**From: Oliver Queen (10:56pm)**

_Come outside. Bring your coat. – Oliver_

Sighing, Felicity reached for the heavy tan peacoat hanging off the back of the front door and pulled it on. As a last-minute addition, she grabbed a crimson scarf draped over the only armchair in the room and wound it round her neck, satisfied that it would keep away any and all chill from the Starling City evening. 

Without giving herself too much time to think too hard about what was to come, she pocketed her phone and keys and willed herself to act more confident than she felt as she padded out into the hall, making sure to lock her front door behind her, and made her way downstairs.

When she reached the front lobby, she stopped.

And stared.

_He wasn’t-?_

_No._

_No way._

_Absolutely not._

Felicity blinked once. Blinked twice. She even rubbed at her eyes under her glasses, convinced that she wasn’t really seeing what she thought was seeing.

Except, of course, she _was_.

Through the glass doors of the main entrance, she could see Oliver standing on the sidewalk, clearly waiting for her. A nearby streetlamp picked out the yellow-gold tones of his short hair and highlighted the smart-looking (and probably very expensive) leather jacket he wore, but otherwise he was mostly in shadow.

A Man of Mystery, indeed.

She thought she might be nervous upon seeing him. Her heart (as well as other parts of her) had a tendency to betray her head when she came face-to-face with him, and this was the first time they were going to be spending any time together aside from the brief encounter in the elevator, the even more brief acquaintance at the gala when she’d smashed an entire crate’s worth of champagne all over his shoes, and then his persistent attempts to ask her out in her office cubicle at Queen Consolidated.

As far as Operation Heartbreaker went, tonight was the make-or-break event. If he didn’t want to see any more after whatever he had planned tonight, she was going to have to throw in the metaphorical towel and admit defeat.

Though she was currently thinking of reconsidering the entire thing as her eyes fell on the gleaming black-and-chrome monstrosity that Oliver had, quite obviously, used as transport to get to her apartment.

_No. Freaking. Way._

There was nothing – _absolutely nothing_ – in the plan she’d agreed to that said she would have to ride a motorcycle.

Apparently, Oliver had other ideas.

Like leading her to her death on the back of a giant, _live_ metal contraption with just two wheels and nothing to protect you if you crashed or were flung over the handlebars like a trapeze artist.

If she died while trying to seduce Oliver Queen, she was _so_ coming back as a ghost to haunt him for the rest of his life.

Her phone buzzed, and she felt her cheeks grow warm as she read the text she had just received.

**From: Oliver Queen (11:03pm)**

_I can see you, you know. – Oliver_

**From: Oliver Queen (11:06pm)**

_Don’t be nervous. – Oliver_

**From: Oliver Queen (11:09pm)**

_Do you trust me? – Oliver_

That gave Felicity pause. Did she _trust_ him? What kind of question was that?

**From: Felicity Smoak (11:11pm)**

_Yes. No. I don’t know._

**From: Oliver Queen (11:12pm)**

_Then let me give you a reason to change your mind. – Oliver_

**From: Felicity Smoak (11:14pm)**

_Okay._

Taking a deep breath to steel her nerves, she shoved her hands into the pockets of her coat and crossed the lobby to the main entrance, where she was greeted by a gust of wind and the sharp cold of the night that reddened her cheeks and nose within seconds.

_Attractive._

She buried her nose in her scarf to keep in the warmth as Oliver greeted her, a blinding smile on his face. He wore only a thin shirt under his jacket and didn’t appear to feel the cold at all.

Felicity hated him for it.

“I wasn’t sure if you were going to bail on me,” he admitted, by way of a greeting. “Thought you might have had second thoughts.”

“I - wasn’t having second thoughts,” she replied quickly. “It’s just…well, it’s really freaking cold out here!”

Oliver laughed good-naturedly, and the sound alone brought back some of the warmth into her fingers and toes. She was lucky she had the excuse of the chill to explain away her rosy cheeks; she didn’t want him to catch on to her embarrassment, or her nervousness.

“You’ll warm up soon enough where we’re going,” Oliver promised. He raised an eyebrow. “Unless you have reservations about the transport?” He indicated the shiny motorcycle.

Felicity gulped.

She could do this. She could definitely do this.

Right?

“A little,” she said nervously.

“Don’t worry, Felicity, you’re in good hands,” he said. “I’ve been riding bikes since I was sixteen. I’ve had this one for five years. I know what I’m doing.”

“ _That_ is five years old?” she sputtered, disbelieving. “But it looks brand new!”

Oliver merely winked, and held out the smaller of two helmets.  She took it, feeling the weight of it in her hands. She’d never held a motorcycle helmet before; it was much heavier than she had expected, and it took a lot of forearm effort just to hold it in both hands. At least she would be getting a workout in.

Felicity pocketed her glasses – she clearly wasn’t going to need them - and slipped the helmet on over her head. Immediately her vision went dark, like she was wearing sunglasses. It was weird, though not so bad as she might have initially thought it was going to be. She blinked through the dark screen of the visor, adjusting the helmet on top of her ponytail.

At least her ears weren’t cold anymore.

“Ready?” Oliver was already sitting astride the motorcycle, his own helmet in place, the visor pushed up so that he could see her properly. He was grinning, and Felicity was almost convinced that this whole thing was still a good idea.

_Almost_.

Gingerly, Felicity climbed onto the back of the bike, feeling it wobble ominously beneath her despite Oliver’s weight holding it in place up front. He twisted round in his seat, his eyes following her as she scrambled into place, and she felt her skin heat under her many layers of clothing. When he gently guided her left leg into position just behind his, his hand warm on her thigh through the denim of her jeans, she thought her face might burst into flame.

It was a good thing she was behind him, and he couldn’t see her face.

Without warning, Oliver turned the key in the ignition and the bike gunned to life with a deafening roar that almost unseated her; instinctively, she grabbed for his waist, her fingers clawing at his jacket, and she blushed even further when her fingers came into contact with the thin material of his shirt. She could feel the thick muscle underneath, and the blazing warmth of his skin, which did wonders for her frostbitten fingertips but not so much wonder for any other part of her.

A part of her that was suddenly very, _very_ interested in this whole endeavour.

“Hold on tight!” he shouted over the roar of the engine, and that was the only warning he gave before steering the bike expertly into the traffic rushing past them, as quick and smooth as a snake moving through the grass.

Felicity shrieked as they joined the dozens of cars, bicycles, and pedestrians on the road, all her concentration directed towards not falling off the bike and smacking her head on the asphalt. _Thank God for the helmet_ , she thought. At least if she fell, she was at much less risk of traumatic brain injury than she would have been without one.

_Sexy, Smoak. Real sexy,_ another part of her brain told her as they whipped along the road, cold air biting at her fingers, and the vibrations of the bike making her legs feel like jelly. _You’re on the back of a motorbike with_ Oliver Queen _. Enjoy it._

But she couldn’t enjoy it if she was too busy worrying about the possibilities of them crashing, or being hit by another vehicle, or whether she would have any bones left after being so thoroughly _jostled_ by the power of the bike underneath her.

So instead, she screwed her eyes shut, tightened the grip of her legs on either side of the bike, and willed herself not to throw up.

They seemed to fly over the road at breakneck speed, the traffic on either side of them a blur of colours and headlights, and it wasn’t long before Felicity noticed that the route they were taking was unfamiliar to her. She could _feel_ where they were going, almost; though she kept her eyes shut, the road felt different, the turns and corners strange.

She wrapped her arms tighter around Oliver’s waist, and she could feel his chest rising and falling with each breath, the contraction of muscles in his stomach as he inhaled and the way his whole body loosened on the exhale, a well-practised rhythm. She wondered whether it was just the result of years spent riding motorcycles, or whether it was something else.

Though she was terrified, Felicity somehow trusted him. But maybe that was just the cold getting to her.

Or it could have been the smell of him, leather and warm skin and expensive cologne, that made her feel somehow safe, despite the fact that she had no idea where they were going and she was expecting to be hurled off the bike at any moment.

Felicity gathered the courage to slowly open one eye, peering around cautiously. They didn’t appear to be anywhere she recognized; if she’d been here before, she certainly didn’t remember it. There was less traffic on the road now, and it was quieter; she could hear her heartbeat in her ears, and Oliver’s gruff breaths. Their surroundings rushed past in a blur of shadows and noise, punctuated here and there by bright lights from an apartment block or a bar that was still open, spilling customers out onto the sidewalk.

And the more she looked, the less scared she felt.

The more she took in, the more she absorbed the environment – the cold of the air, the streetlamps, the shouts of one group of people to another, the cars on the road, looking as slow as turtles compared to _their_ speed – the more she felt less terrified and more… _alive_.

Maybe Oliver _wasn’t_ a maniac with a death-wish after all.

Felicity opened both her eyes, determined to take in as much as she could through the dark screen of the visor that covered her face. Instead of focusing on what could go wrong, and thus worrying herself to pieces, she focused on the howl of the wind in her ears and the force of the machine, pushing them forward. Instead of letting the vibrations of the bike rattle her bones, she allowed the sensation to fill her up, her blood singing with adrenaline, and her muscles buzzing with the effort of holding on. Her arms ached where she kept a vice-like grip on Oliver’s waist, but she barely noticed; instead of feeling like she might fall off if she let go, she used his body like an anchor as the rest of her flew.

And boy, did she _love_ flying.

“This is so awesome!” she yelled, to nobody in particular; she just wanted to get the words out, to feel her chest constrict with lungfuls of biting cold air, to feel the sting of the wind on her neck where her scarf had slipped, to feel the prickle of numbness beginning in her thighs and the tickle of her flyaway hair against her cheek.

She felt the rumble of Oliver’s amusement beneath her hands, and she blushed. But right now, she didn’t care.

She really, really didn’t care.

It felt _amazing,_ and she never wanted it to stop.

But, alas, it _did_ stop; Oliver suddenly slowed and veered out of the flow of traffic to pull the bike over to the side of the road, bringing it to sharp stop outside a small twenty-four hour diner that Felicity had never seen before. The bright light coming from the front of the place made Felicity blink rapidly, even under the visor, and her heart was still slamming against her ribs as Oliver took the key from the ignition and sat back, taking off his helmet to scrub a hand through his short hair.

Felicity saw the callouses on his fingers, and wondered what it would be like to feel those fingers on her bare skin.

She shook her head to clear such thoughts, moving to unsnap her own helmet with heavy breaths, her arms and legs tingling with adrenaline.  

Had she really just ridden on the back of a motorcycle with Oliver _freaking_ Queen?

Yes. Yes, she had.

“Still feel nervous?” Oliver asked, grinning.

“No,” Felicity panted, smoothing out the end of her ponytail and pulling her scarf down around her neck so the night air could chill her flushed face. “You know, at first, I thought you were trying to kill me, but I think I liked the adrenaline rush.”

“I don’t kill pretty women on the first date,” Oliver reassured her, his lips quirked in a small smile.  “You’re in safe hands, Felicity.”

Felicity gulped, her mind lingering on the way he said her name, _Felicity_ , the hard ‘F’ and the stress on the syllables. _Fe-li-ci-ty_.  She adjusted and re-adjusted her scarf agitatedly, distracting herself with the feel of the wool between her fingers.  When she spoke, her voice was a croak. “This is our first date?”

“Yes,” Oliver nodded. His voice softened as he continued, “If you want it to be.”

The deference he showed to her authority surprised her; she would have expected _him_ to be the one calling the shots.

“I want it to be,” Felicity affirmed.

For a few moments, they sat in silence, the cold wind whipping across their faces, and then suddenly Oliver dismounted from the bike, tucking his helmet under his arm. The unexpected movement made the machine wobble slightly, and Felicity scrambled for purchase on the soft leather seating, steadying herself.

“C’mon, it’s cold out here. And I promised to tell you where the best coffee in Starling City was,” Oliver said, holding out his hand in a gesture that he meant for her to take it.

And, well, who was she to refuse?

It was all part of the plan, after all.

“Lead the way,” she replied with a smile.


	8. Chapter 8

**Summary for the Chapter:**

> AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.
> 
> Written for the Olicity Fic Bang 2015.

**Notes for the Chapter:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning.
> 
> [Listen to _How To Be A Heartbreaker:_ The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

* * *

**Playlist for this chapter:**

1.  _XO_ \- Beyonce

2.  _Hands To Myself_ \- Selena Gomez

3.  _Power and Control_ \- Marina and The Diamonds

* * *

Her alarm blared, loud and buzzing and _definitely_ unwelcome, at 6:10am that morning while Felicity was half-in, half-out of a deep, deep sleep.

Had last night been a dream?

She half-heartedly threw a slipper at her alarm clock, cutting it off mid-buzz. It was too _early_. Why was it so _early?_

Dragging herself out of bed, Felicity retrieved the thrown slipper and pulled it on, along with its matching partner, not even bothering to cover the huge yawn that escaped her as she did so. She stretched her arms above her head, shaking out her sore muscles and feeling the bones in her shoulders and back crack with the strain.  She was tired, sure - bone-tired, in fact - but she didn’t feel sluggish or _exhausted_ in the usual way that people felt when woken abruptly at 6am. In fact, she felt quite the opposite. She felt _content._

It wasn’t until she trudged over to her small bathroom to wipe away the remains of last night’s mascara and brush her teeth that she realized why.

Her lips were red and chapped, puffy around the edges, and the memory of last night – well, a few hours ago, she supposed – came flooding back to her.

_When the diner had finally shut its doors just after 1:30am, they’d finished the last dregs of their coffee and left the brightly-lit and, more importantly, warm interior to wander arm-in-arm around the block for a while. It had felt odd at first, Felicity very conscious of Oliver at her side, and she’d had to quicken her pace a little to keep up with his longer strides.  When he noticed her struggling, he’d slowed down, pulling her closer to his side, and the urge to fit herself under his arm and leach some extra warmth from his body had almost overwhelmed her._

_She’d resisted, though, and tried to keep her thoughts (and her heartbeat) in check as they’d returned to the bike and pulled apart from one another, though she had felt Oliver’s eyes on her until the very last moment when she clicked the visor of her helmet into place and they could no longer see each other directly._

_The ride back to her apartment really had felt like flying, now that she was alive to the raw power and exhilaration that came with travelling at such speeds, in the dead of night,  under the few stars that pricked the intense blue-black of the sky._

_It was also over much too soon._

_Oliver parked the motorcycle just outside Felicity’s apartment building, in almost the same place he’d been waiting for her several hours earlier._

_The doorman on his night shift was waiting patiently just inside the double doors, the interior of the lobby mostly dark except for a few circles of light cast by tall floor lamps. She’d never returned to her building this late before. It was eerie, seeing the empty space, the dim light glinting off the row of metal mailboxes along one wall. Like a ghost building._

_She told him so, to fill the silence in the absence of the roar of the bike and the rush of wind past her ears. The lack of noise felt strange to her now, when it had been all she could hear just minutes ago. “This is so weird. I’ve never come back to my apartment this late before.”_

_“So I’m a bad influence on you?” Oliver asked. It made her feel strangely warm and fuzzy inside, like being cocooned in a soft blanket._

_Felicity smiled back, feeling suddenly shy and trying to tamp down the squirminess of her insides. “I guess you could say that. What time_ is _it, anyway?”_

_Oliver looked at the watch she now noticed that he wore on his right wrist. It surprised her to see that it wasn’t one of those ostentatious, uber-expensive watches she often saw rich and powerful men wear. It was actually rather plain and functional, not what she had expected for a man of his socio-economic status. “Almost 3am.”_

_“Isn’t that, like, an ordinary bedtime for you?,” Felicity joked, before she could stop herself, and_ oh _, that was a bad idea, because now she was thinking about Oliver and beds and the things he liked to_ do _in his bed and with_ whom _he liked to do such things, and that made her think about what_ she _might have to do_ with him _, in his bed. Because it was part of the plan._

_The Plan To Make Oliver Queen Fall In Love With Her._

_That plan._

_Thankfully, Oliver took the quip good-naturedly and joked back at her, “You really don’t know that much about me, do you?”_

_“No, I don’t,” Felicity admitted. “But I want to.”_

Smooth.

That was _really_ smooth.

Surprisingly smooth, actually.

_She was fairly impressed with herself. That was definitely going on the blog later._

_The warm, fuzzy, squirmy feeling came back as they both looked at each other for a long moment, Felicity clenching and unclenching her fists in the pockets of her coat._

_“We should say goodnight,” Felicity said. “I mean, I do have to be at work in six hours, so...”_

_“If I didn’t know better, I’d say you were trying to get rid of me,” he teased. Why did everything he said always sound so…playful? It confused her.  Did he even have a serious bone in his body?_

_“I’m not trying to get rid of you,” she replied, as sincerely as she could. “I just don’t think my boss would accept ‘midnight motorcycle ride with a male suitor’ as an excuse for not coming into work – well, I was going to say tomorrow, but it’s already tomorrow, so….today. It wouldn’t be an excuse for not coming into work_ today _.”_

_“Which is in six hours,” Oliver nodded in confirmation._

_“Exactly.”_

_Felicity bit her lip, suddenly pretending to be very interested in her shoes. She could feel the tips of her toes and fingers prickling with cold, and she longed to be back inside her warm apartment (and her very warm bed), and yet…it wouldn’t be right to just turn around and leave._

_She’d….had a pretty amazing night, actually. And it was thanks to him._

_“So, I, uh, guess I should wish you goodnight,” Felicity stammered. “Or maybe ‘good morning’ would be more appropriate?”_

_“The sun isn’t up yet, so I think we can get away with wishing each other goodnight,” Oliver said._

_“Okay,” Felicity agreed. “Goodnight, then.”_

_“Goodnight, Felicity,” Oliver said softly._

_She turned to leave, ponytail bobbing in the air, before he suddenly caught her wrist and spun her back around, his fingers warm on the tender skin of her wrist._

_He spoke so quietly she almost didn’t hear him. “I forgot to do this…”_

_And then he closed the gap between them, capturing her lips with his warm mouth in a slow, deliberate kiss that made her face flush and her eyes slip closed of their own accord, a hum of pleasure on the tip of her tongue and her fingers twitching in mid-air where he grasped her wrist, itching to touch, to hold, to_ feel _._

_It was, quite possibly, the best goodnight kiss she had had in a long, long while._

_When he moved away, she found herself licking her own lips almost without thinking, to chase the taste of coffee and wintry air left behind by his mouth._

Holy crap.

_“That was….” Felicity stuttered breathlessly, “Um. Wow.”_

_“Some kiss, right?” Oliver said, and his face was inches from hers, eyes bright and intense in the dwindling moonlight – morning was coming, and the sky was rapidly turning from the colour of the ocean to the colour of a lake in the sunshine, and somehow his eyes were the same shade of brilliant blue as the vast expanse of nothingness above them._

_It sort of took her breath away._

_“You are so full of yourself,” she snorted, effectively shattering the spell of the moment and bringing her firmly back to reality._

_And that reality was that she had to be up for work in just over 3 hours and unless she was in her bed really,_ really _soon, she wouldn’t be going into work at all._

_Nonplussed, Oliver quickly pressed his mouth to hers in a second, chaste kiss, before letting go of her wrist and watching her retreating back as she turned and went inside her apartment building._

Felicity pressed her fingers to the edges of her kiss-swollen lips, remembering what it had been like to have his mouth on hers. How warm it had been; how he had tasted. If she didn’t have physical proof right there in her reflection in the mirror, she would have found it hard to believe that it had ever happened at all.

Three hours ago? It felt more like three minutes.

And she had to leave for work soon and pretend like her midnight rendezvous with Oliver had never happened.

Fat chance of that.

While she dressed, she opened up her laptop and went to the now-familiar hot pink homepage for the Operation Heartbreaker blog. It was better to get the details down now, while she still remembered them, and wasn’t _so_ tired that she had completely forgotten how to use a keyboard.

(Though she was fast approaching that stage, and would definitely need coffee once she got to QC. Lots and lots of coffee.)

She was trying to decide whether to describe Oliver’s lips as _soft and luscious_ or _warm and inviting_ (for the sole purpose of recording _all_ the details, naturally) when she fell asleep halfway through applying her make-up and woke up twenty minutes later with one eye made-up and the other completely bare to the knowledge that she was going to be late for work.

_Again._

Damn Oliver Queen and his soft, luscious, warm, inviting lips.

Smoothing her hair into a low ponytail (she didn’t have the time that morning to scrape it up into a high one, and quite frankly, she was too tired to attempt it anyway) and pulling on a coral cardigan over the pale lavender dress she had chosen to wear that day, she just had time to add fuchsia lipstick and buckle her feet into black shoes before she was in her car and on the road again.

She really did need to learn to be more punctual.

Then again, it was probably more to do with the fact that she was running on three hours of sleep and was currently un-caffeinated than any character flaw that made her tardy at least once a week.

Upon reaching Queen Consolidated, she hurried through the lobby and up to the IT Department, fully intending to find a cup of coffee or five as soon as she could dump her bag at her desk, but, _oh_ , the Fates seemed to be smiling down on her that day despite her lateness, because when she reached her desk, she discovered that the issue of caffeine had already been taken care of.

The Fates, apparently, took the form of Oliver Queen.

_Consider this an apology for dragging you out of your apartment in the middle of the night :)_ read the fluorescent orange Post-It note stuck to the cup of steaming coffee standing on her desk, the same coffee that they had drunk last night at the cute diner on the outskirts of the Glades, the diner that made the best coffee in Starling City.

If Oliver had been there right at that very moment, she would have kissed him again, propriety be damned, because this might just have been the best thing he’d done since they’d met fourteen days ago.

_It’s also proof that he’s sweet on you_ , she thought to herself as she took a grateful sip of the strong, sweet beverage. _Which is good for The Plan. That can’t hurt, either._

And it certainly didn’t, not right then, because she was too busy making up for lost time by indulging in wonderful, wonderful caffeine and reading work e-mails to think of anything else but shaking the tiredness from her system and getting ready to face the day.

 ***

**From: Tommy Merlyn (11:31am)**

_I know this great place in the Glades that would be perfect for tonight._

**From: Laurel Lance (11:32am)**

_I’m at work, Tommy. I can’t do this right now._

**From: Tommy Merlyn (11:36am)**

_Is that your special way of telling me that I’m free to pick which restaurant we eat at for our date?_

**From: Laurel Lance (11:38am)**

_If it makes you happy, Merlyn, then yes._

**From: Tommy Merlyn (11:40am)**

_Yes!_

**From: Laurel Lance (11:42am)**

_You are such a dork._

**From: Tommy Merlyn (11:43am)**

_And don’t you ever forget it :)_

_***_

By the time lunchtime rolled around, Felicity no longer felt her exhaustion in her bones, though staring at her computer screen for too long did make her eyelids droop every so often; when this happened, she had taken to snapping her wrist with an elastic band that was lying on her desk to make sure she didn’t actually fall back to sleep.

She was still thinking about the kiss, and the motorcycle ride, and best coffee in Starling City, and strolling around the outskirts of the Glades under the stars, and had been for most of that morning.

It was making it difficult for her to concentrate on almost anything else.

Honestly? Felicity hadn’t expected that Oliver would have such an effect on her, and she didn’t really know what to think about it.

Yes, he was ridiculously attractive, and yes, he was a phenomenal kisser, and yes, he _did_ have the cutest smile of anybody she’d ever met – but he said things, did things, that reminded her of the spoiled brat he’d grown up as, and the shallow rich asshole that he still was. That he still could be, when he wanted to be.

Why did such a hot person have to have such an irritating personality? And why did he have to be so contradictory? Would it kill him to just be straight with her? It would make _her_ job, getting him to fall for her, that much easier if he wasn’t so damned hard to figure out. Cute and charming one day, glib and crass the next. She was surprised he hadn’t tried to proposition her for sex yet. She wasn’t sure what it meant that he hadn’t.

The point was, he _had_ surprised her. And she wasn’t entirely sure what she was supposed to do about it. Stick with her original plan? Change tactics somehow? Even if she did go with the second option, what would she change her tactics _to_?

They’d had one date. And if the goodnight kiss was anything to go by, he wanted another. It just so happened that the ball was now in his court; if she seemed too forward, he might suspect something. She had to give the man _some_ kind of agency in all of this. It was only polite.

_Says the girl planning to dump his ass the minute he gets down on one knee_ , she thought to herself.

When did she get so…ruthless?

Her Mom would be proud.

Felicity went to drain the last of her coffee (her third dose of the good stuff that day), only to discover that her mug was already empty – when had she drank it? She couldn’t remember. She’d been so focused on her work, practically on autopilot, that she’d never noticed.

She glanced at the clock on her computer screen, tapping her nails on the rim of her mug. It was 1:35pm. High time for a refill. She didn’t have anything urgent to do, anyway. Her supervisor would forgive her for getting a (fourth) cup of coffee.

Though, in her defence, the first one had been a gift.

Grabbing her mug, she made her way out of the small corner cubicle she called home (at least between the hours of nine and five each day) and in the direction of the break room, which was down the hall from the main offices of the IT Department and the sole source of any and all exercise she got on a weekly basis.

That, and forcing herself to do 40 minutes twice-weekly on an elliptical machine, because she liked her small waist and wanted to keep it, excessive coffee and mint-chip ice cream notwithstanding.

Little did she know, there was a surprise waiting for her.

A surprise that made her shriek in an unladylike manner as a familiar hand with warm, calloused fingers seized her wrist just as she was passing the end of the elevator bank that filled one side of the hall, and she found herself dragged backwards and _into_ one of the elevators, her favourite chunky blue mug slipping from her fingers and thudding onto the carpet just before the doors slid closed behind her.

“So, no fourth cup of coffee, then,” Felicity muttered to herself in lamentation, and she heard Oliver chuckle somewhere above her head as he tightened the arm currently wrapped around her waist, forcing her further up against his very broad, very _solid_ chest.

She glanced down – and she could see the outline of Oliver’s pecs through the white shirt he was wearing.

Her throat went dry.

It was suddenly very warm in the small space, the combined heat of their bodies making the temperature rise where she was pressed flush to his body, and she vaguely noticed that his suit was a darker grey than before, slate instead of dove, when he kissed her hungrily, his grip on her waist impossibly tight. The angle, not to mention the difference in their heights, forced her to bend backwards to receive the kiss, and her hands came up instinctively to cup either side of his face. His skin was warm under her fingers, the feeling of smooth cheeks giving way to a stubbled jaw sending a thrill of anticipation up her spine and warmth to her very core; she had never expected facial hair to be a _thing_ for her, but apparently it was, as her thumbs brushed the prickle of a couple days’ growth and Oliver gasped into her mouth, quiet and breathless. It wasn’t slow, or soft, or gentle; it was rough and heated, her lipstick smearing and Oliver’s mouth as hot as a flame, his strong grip holding her in place.

It was nothing like their kiss just hours earlier, and Felicity was both afraid of and thrilled by it.

The elevator began moving upwards, taking them to the very top floor of the building, but neither of them noticed the movement under their feet or the smooth glide of the elevator shaft up, up, up, too engrossed were they in each other and in exploring each other’s mouths. Felicity moved her hands from his face to his biceps, gripping the swells of muscle tight as she allowed Oliver to lick into her mouth with his tongue, tracing her lips before pressing in and wasting no time in deepening the kiss further. Felicity’s glasses were knocked aside; they fell to the floor at her feet, forgotten, and later she would wonder how she managed _not_ to step on them, consumed as she was by lust and the sheer pull of, well, _Oliver._

_Oh God, oh God, oh God_.

Her hands didn’t know what to do with themselves, and she patted his arms and chest uselessly as she babbled, “You’re so – you’re so strong,” her breath coming out in embarrassingly harsh pants. He grinned against her mouth, impossibly wide, and she could see the imprint of her lipstick at the corners of his own lips; it sent another flash of heat through her, coming to rest in the pit of her stomach, where something not unlike arousal was pooling deep within her.

Judging by the blown look of his pupils, pitch black against the deep blue of the irises, he was in the same situation that she was.

Oliver glanced up towards the digital screen in the corner of the elevator, displaying the number of the floor they were on. Felicity followed his gaze. Number twenty-six.

“We have plenty of time,” Felicity panted. Her mind screamed at her; _what are you doing? You’re not an exhibitionist!_ But her body, her heaving chest and racing heart, told her something else.

It told her, _to hell with it._

“Yes, we do,” he affirmed, and the same kind of raw hunger came over his features again as he returned to her mouth, this time wrapping both arms around her waist and almost lifting her from the floor in his eagerness, and she found herself gripping his broad shoulders just to hold on, swept up in heat of the moment.

She wasn’t thinking about Operation Heartbreaker when she caressed his tongue with her own, forcing their mouths open, their lips almost bruising with the intensity of the kiss.

She wasn’t thinking about Operation Heartbreaker when his large hands found her ass through the material of her dress, fingers applying just that little bit of pressure to make her squeak, high in her throat, and a moan fall from her lips before she could stop it.

She wasn’t thinking about any kind of plan at all when Oliver suddenly lifted her as if she weighed less than a feather and her legs instinctively locked around his waist, his mouth finding her throat and her name nothing more than a mumble of lips and tongue against her skin, _Felicity, Felicity, Felicity_ , which made her heart stop and her blood race, her underarms damp with sweat and her cardigan too hot against her sensitive skin.

He pressed her back against one wall, depositing her on the brass handrail that ran along the sides of the elevator, and she crossed her ankles against the small of his back to anchor herself as he continued to press hot, open-mouthed kisses along the column of her throat, up to her jaw and back down again as if he were trying to memorize the path he was taking and the taste and feel and smell of her skin.

_This is insane_ , her brain told her.

_It also feels really, really good_ , said a little voice somewhere in the part of her mind that controlled the arousal that was fast pooling between her thighs.

The ridge of her ponytail was pressing uncomfortably into the base of her skull, and the bar of the handrail was cutting into her ass, but she hardly noticed. Or rather, she noticed, but simply didn’t care, because it felt so damn incredible to have Oliver pressed up against her like this, hovering over her the way he was, his hands roaming her body and his lips on every inch of her skin he could reach, her face, her neck, the hollow of her throat.

The tops of her breasts where they swelled over the neckline of her dress, the tip of his tongue coming out to flick briefly between them before leaving rosy pink marks on her pale skin from his sucking kisses, and if Felicity had thought that it was insane before, she _definitely_ thought so now.

It didn’t stop her from tipping her head back against the cool wood panelling under her back and moaning, the heels of her shoes digging into his back and the prickle of his stubble ticking at the underside of her chin and jaw, scraping across her throat and cheek, anywhere and everywhere, all at once.

She felt herself throb, her blood pulsing like a hammer between her legs, but she couldn’t press her thighs together to relieve the pressure. Not this time.

She pushed her aching core against the front of his pants instead, and moaned again when she got the relief she so desired – and when she felt him, hard and unforgiving, right up against the apex of her thighs.

She, Felicity Smoak, had given Oliver Queen an erection.

_Wow._

Just… _wow._

“We should – we should stop,” Felicity said breathlessly, her chest heaving. Her fingers slipped on the wood under her hands, her palms sticky with sweat, and her legs were beginning to ache from being suspended in mid-air.

“Do you want to stop?” Oliver asked, low and rough, nipping at her earlobe. He caught the stud of her earring with his tongue, pulling on it oh-so-gently. The soft tug sent a jolt of pleasure through her, and Felicity shook her head vigorously in response to his question.

No, she didn’t want to stop.

Yes, it was probably a bad idea if they didn’t.

No, she didn’t care.

Oliver pulled away suddenly, and the rush of cool air above her in the absence of his body almost made her whimper pathetically. She was so hot, so highly-strung, so…

Dammit, she was turned on. Very, very turned on.

And then he dropped to his knees between her legs and she barely swallowed down a gasp before his lips were on her trembling thighs and she forgot everything except his own name, which she babbled, over and over again, unable to stop herself.

“Oliver,” she gasped, gripping the bar under her ass so tight her knuckles turned white, “oh my God, Oliver…”

It was hell.

It was heaven.

It was everything in between.

If she’d had her wits about her, she’d have been more worried about the possibility of oral sex in an elevator where any one of her fellow QC employees could have found them.

She would also have been more worried about what it meant in the grand scheme of things that spending just a few hours with him over the space of two weeks had her garbling Oliver’s name nonsensically while she so willingly spread her legs wider, wider, wider, allowing him better access to the sensitive skin of her thighs and what would by now be her very, very damp panties.

When she’d agreed to this plan, she’d swore she wouldn’t be “that girl”. That she would do this the right way. That she wasn’t going to be his average conquest. That she wouldn’t submit so willingly to his charms. That she would keep a cool head.

This was, after all, about revenge, not pleasure.

Apparently, her vagina had other ideas.

“I want to see you tonight,” Oliver said, in between peppering her right thigh with kisses. “Let me take you to dinner.”

“Didn’t we already just – oh God – go on one date?” Felicity countered, biting her lip to keep back the moan building in her chest.

“Please, Felicity,” he murmured. “I need to see you again. At least once every twenty-four hours, if I can.”

“Stalker,” she snorted, but secretly she flushed with pleasure at knowing that she had him in the palm of her hand. He was practically begging to see her. This was what she wanted.

“Not stalking,” Oliver muttered, moving across to her other thigh, “Just want to see you.”

_I bet you tell that to all the girls_ , was the reply on the tip of her tongue; but she forgot her words when he nosed gently at her panty-clad entrance, the fabric pushing up against _that_ little nub and she cried out, gasping, embarrassingly loud in the small space.

Damn him.

He grinned against her skin, satisfied. “Is that a yes to dinner?”

“Just as – _ah_ , oh my God – as long as it’s Italian,” Felicity said, as he repeated the motion, sending shockwaves of pleasure through her blood, burning like fire under her skin. “I like Italian.”

“I think I can make that happen.”

She opened her mouth to say something else – to moan, to gasp, to make _some_ kind of noise – but the elevator suddenly rolled to a stop.

They’d reached the top floor of the Queen Consolidated building.

When had they reached the top floor of the Queen Consolidated building?

How had neither of them noticed how many floors they’d travelled upwards?

“I think our time’s up,” Oliver remarked, drawing away from between Felicity’s legs. She clamped her thighs together in his absence, another pulse of pleasure rushing through her.

“If I try to stand, I might fall over,” she groaned. “I’m so horny right now I can’t feel my legs….and I actually just said that. Out loud.” Cheeks pinking, she peeked at Oliver through one open eye. “You still want to take me to dinner after what I just said, right?”

“It would be my pleasure,” he asserted, smiling like he hadn’t just been busy between her thighs just moments earlier.

“Help me down from this rail?” she asked, extending one hand towards him. He obliged, sliding one arm around her waist and gently lifting her up and off the bar, setting her back down on her feet. The friction of her kiss-marked thighs rubbing together was enough to make her almost moan again, but she pushed down the feeling and tried to steady the frantic beating of her heart, her breaths slowly returning to normal.

Pushing the skirt of her dress back down and reaching for her fallen glasses, a somewhat awkward silence stretched between them.

What did one say after being kissed into oblivion by a man they’d only really just met?

She doubted that “Thank you for almost giving me an orgasm in your father’s company’s elevator” would be the appropriate sentiment.

“I should – get back to work,” Felicity said, smoothing down the edges of her dress and attempting to re-button her cardigan, which would have worked better if her fingers weren’t still shaking a little from the intensity of the pleasure she had received. “Are you…?” she gestured vaguely in the direction of his lower half, face flaming, having noticed that he was still a little hard. And neither of them had actually, well. Y’know. _Come._

Oliver huffed out a nervous laugh, biting at his bottom lip. “I guess I’ll, uh, need to take a cold shower after this.”

“Good luck with that. Oh, God! I did it again. Please, just stop me from talking altogether.”

The elevator pinged, and the doors slid open. Walter Steele got in.

“I didn’t realize you were visiting your father today, Oliver,” he commented, surprise evident on his face as he went to stand next to him.

“Uh, yes. Yes, I am. It was an….impromptu decision,” Oliver replied smoothly. When Mr. Steele wasn’t looking, he winked in Felicity’s direction. She blushed fiercely.

_Impromptu, indeed._

“And Miss Smoak! I almost didn’t see you there. How are you finding your work at Queen Consolidated?”

Felicity froze, not expecting to have been addressed so directly. Quickly, she came up with something believable to tell him. “Everything’s going great, Mr. Steele. Sir.”

“Good. I’m glad to hear it.” He turned to Oliver. “Well, I suppose you’ll be wanting to see your father, so I won’t keep you. It was nice to see you, Oliver.”

“You too, Walter.”

Felicity could tell that the pleasantries were only partly genuine; he, like her, wanted to get out of a potentially awkward situation. It wouldn’t have been unusual for him to be found in the company of a Queen Consolidated employee, but unexpected all the same. The fact that they had been seen together at all was a red flag.

As Oliver exited the elevator, leaving Felicity alone with Mr. Steele, she felt…uncomfortable. Nervous. And not just because she was still so very turned on.  

She didn’t want the plan to be ruined just because she – _they_ – had been careless.

As it was, they rode back down in silence. Felicity exited the elevator when it reached the IT Department, gratefully leaving Mr. Steele behind. She quickly re-touched her lipstick in the women’s bathroom and then returned to her desk, feeling the pleasurable burn on her thighs where Oliver’s stubble had scratched at the skin for the rest of the afternoon.

 ***

 “Okay, tell me again, _slowly_ , what happened between you and Oliver this afternoon,” McKenna said, indicating the notepad she was currently holding. “I need details, girl. You already went on one date with him without telling us, and now need to make up for that. Spill.”

Felicity sighed. She supposed she should have been expecting the ambush; it had been a while since she’d communicated anything related to Operation Heartbreaker to her friends, aside from Laurel, and they were out of the loop.

Still, she didn’t think they needed to know _everything_. She could withhold a little and still tell the truth, couldn’t she?

She gratefully accepted a glass of wine from Sara, and took a sip to calm her nerves before she spoke again. “We made out. In the elevator. At Queen Consolidated. Actually, he kidnapped me – it’s a long story,” she added quickly, when her friends’ eyes went wide in shock, “I was going to get coffee because I’d ran out and I was already _exhausted_ from being out all night with him and…” She stopped, taking a much larger gulp of wine. The warmth of the alcohol bloomed in her chest, a welcome distraction from what she felt was an interrogation. Felicity wrinkled her nose, a shudder going through her. “It sounds really slutty, doesn’t it?”  

“No!”

“Of course not.”

“Absolutely not.”

“Of course it’s not.”

Felicity looked around at her group of friends, from Laurel to McKenna to Carly, to Sandra and Sara, assessing their far too eager chorusing of the negative with a judgemental eye. “You all suck at lying.”

“Okay, so it’s a little slutty,” Carly conceded with a shrug. “So what? At least nobody saw you. It’s lucky they don’t have security cameras in their elevators.”

Felicity had to admit, she had a point. There was nothing wrong with having a little bit of fun. And it had felt so _good_ ….

“Do you know how amazing it is to have him between your thighs?” she suddenly blurted, courage seizing her; her mouth moved before her thoughts could catch up to it, wanting to reveal all the details before she became shy and embarrassed again, even in front of the friends she’d known for years.  “Because I am telling you, it was probably the best non-orgasm I have ever had in my life.”

Her friends goggled at her, as if she had two heads. Five pairs of eyes, disbelieving, looking her up and down, torn between being impressed and slightly worried for her sanity.

Sara let out a low whistle. “Damn, Smoak. Who knew you had it in you?”

“Are you sure you’ve only had one glass of wine?” Laurel giggled.

“We’re going on another date tonight,” Felicity confided, sipping at her wine. “An actual dinner-date, this time. At a restaurant. Obviously. An _Italian_ restaurant.”

“Because you like Italian,” Sara provided, nodding in confirmation.

“Yep,” Felicity replied, popping her lips on the ‘p’. “Can I say something? I’m actually _excited_ about it. Other than the whole ‘make Oliver fall in love with me and then dump him’, thing. I actually really want to go.”

“Uh-oh,” McKenna said, holding up a hand. “You don’t actually _like_ him, do you? ‘Cause that’s not what we agreed.”

“No! God, no!” Felicity protested, shaking her head. “I mean, yeah, the man looks like a catwalk model and is a really, _really_ phenomenal kisser, and he can be charming when he wants to be, but – he’s hot, but not all that great when it comes to being smart, or, y’know, an actual human being who is respectful of women.”

“But he’s been nothing but nice to _you_ ,” Sandra pointed out. “He hasn’t done anything gross or tried to make a pass at you.”

“ _Yet_ ,” Felicity emphasized. “I like looking at him. And he’s nice, most of the time. It’s fun with him. And it’s even more fun knowing that I have to end it in just over a month and I get to see the look on his face knowing he’s been set up.”

At that moment, her cellphone buzzed. When she saw who it was, she grinned around another mouthful of wine. “Speak of the devil.”

**From: Oliver Queen (6:30pm)**

_How does 8 work for you?_

“Let me see!” Carly half-shouted in her excitement, reaching for Felicity’s phone. “He’s actually asking you what time you want to go to dinner? Wow, he must really like you. Andy never lets me choose what time we eat when we go out on dates. It’s sweet that he wants to take care of me, but I can do things for myself, y’know?”

“If you don’t give me my phone back, I can’t reply, and then we won’t be going out at all,” Felicity pointed out. “And really? Andy never lets you choose what time you go out?”

Carly shrugged. “What can I say? He’s a gentleman, but a little old-fashioned sometimes. It’s the army in him, I think. Military code of honour and all of that.”

“My _phone_?” Felicity pressed, stretching out her hand impatiently.

Carly handed it back. Downing the last of the wine in her glass, Felicity texted Oliver back.

**From: Felicity Smoak (6:33pm)**

_8 would be excellent. Do I get to know where we’re going?_

A few moments later, she received a reply.

**From: Oliver Queen (6:34pm)**

_If I say no, will you be mad at me?_

**From: Felicity Smoak (6:35pm)**

_That depends. I have a really bad nut allergy. Are you willing to accommodate that?_

**From: Oliver Queen (6:37pm)**

_For you? Absolutely._

“Awwwww,” Carly cooed, reading over Felicity’s shoulder. She startled, quickly turning off the screen of her phone.  

“You know it’s rude to spy on people while they’re reading _private_ texts, right?” she said pointedly, fixing the rest of her friends with a withering stare. “And that applies to all of you, too.”

McKenna and Sara put up their hands in a gesture of mock surrender; Carly moved from behind the couch (and her position lurking over Felicity’s shoulder) to sit on the floor by the coffee table, folding her long legs underneath her. She sipped at her forgotten glass of wine, giving Felicity a smug smile over the rim of it.

_With friends like these, who really needs enemies, or common sense?_ Felicity thought, gripping her phone too tightly in her hand. She pressed the cool screen against her chin, thinking about what to say next. Flirting was harder over text; you couldn’t read the other person’s expression, or hear their tone. But talking face-to-face wasn’t exactly a walk in the park for her either.

Dammit. She was going to throw caution to the wind.

Felicity opened a new message, fingers hovering over the keypad – but was far too aware of her friends’ eyes on her, watching her every move, and she froze.

“Okay, I can’t do this if you’re all staring at me, it’s weird,” Felicity said, putting her phone aside. She rubbed at the bridge of her nose under her glasses. “Please don’t take this the wrong way, but I need you all to leave. Like, now.”

“You heard the girl,” Carly said, getting up from the floor, “she needs some alone time to get it on with her man.”

“Okay, he’s not my _man_ -“ Felicity began to protest, but Carly winked at her, and the others followed suit, getting up from the couch and armchairs and making towards the door of her apartment.

“Have fun tonight,” McKenna said. “Don’t do anything I wouldn’t do.”

“You’re a police officer. Anything you wouldn’t do is illegal.”

McKenna smirked. “Exactly.”

Felicity resisted the urge to groan, putting her head in her hands. The door banged shut; she heard the laughter and chatter of her friends receding down the hallway, and with it, the tension in her chest that came from being under their watchful scrutiny.

Yes, she knew that they were trying to help her. This had been _their_ plan, after all. And she was grateful for their support. But trying to woo someone when you had five excitable women breathing down your neck wasn’t exactly easy.

Felicity picked up her phone again.

**From: Felicity Smoak (6:46pm)**

_A man after my own heart ;) (And the proper use of my throat.)_

**From: Felicity Smoak (6:43pm)**

_Oh, God._

**From: Felicity Smoak (6:44pm)**

_That wasn’t a blowjob joke._

**From: Felicity Smoak (6:46pm)**

_I wasn’t insinuating that I was going to blow you._

**From: Felicity Smoak (6:47pm)**

_My throat swells up when I eat peanuts. That’s what I was referring to._

**From: Felicity Smoak (6:49pm)**

_Please ignore this entire conversation. Dinner at 8 is perfect. I’ll see you then._

**Notes for the Chapter:**

> Survey question: 
> 
> How are y'all enjoying the playlist that accompanies this fic? Has it helped you enjoy and understand the story? Does it bring something extra to your experience of the fic? How? Do let me know when you leave a comment! I'm curious :)


	9. Chapter 9

**Summary for the Chapter:**

> AU. Felicity Smoak has one simple mission; to make Oliver Queen, heir to the CEO of Queen Consolidated, fall in love with her and propose in just 60 days. There's just one catch - at the end of the 60 days, she has to hand back the ring and break his heart.
> 
> Written for the Olicity Fic Bang 2015.

**Notes for the Chapter:**

> The art for this fic was created by coffee-with-sunshine, who has been putting together an awesome playlist to accompany the story. Each chapter has its own mini playlist, which can be listened to individually, or you can listen to the whole thing from the beginning
> 
> [Listen to _How To Be A Heartbreaker_ : The Playlist on Spotify](https://play.spotify.com/user/ivettealejandra/playlist/1WnLl1xTgSWy3VsOcn4W43)

* * *

**Playlist for this chapter:**

1.   _Dancing On Glass_ \- St. Lucia 

2\. _After Tonight_ \- Justin Nozuka

3. _Stressed Out_ \- Twenty One Pilots

* * *

 

Dinner, as it turned out, was even better than the appetizer she had received that afternoon in the elevator at Queen Consolidated.

When she’d first started this, she’d thought that Oliver’s ways of wooing a woman were unimpressive; superficially charming at best, and crass at worst, she hadn’t found much to commend in his methods or his style. ****

She was slowly beginning to change her mind.

Felicity had picked out a simple dress in a striking red as her outfit for the night, paired with strappy black heels and matching fringed shawl that she would wrap around her shoulders to keep out the chill. She knew that she could have worn a coat, but she didn’t want the bulk of it to cover up the effect of the dress. The point was to draw Oliver’s attention, and since when had any man been able to resist a woman in red? She was counting on him to follow that particular trend among the male population.

Somehow, she didn’t think he’d disappoint.

Deciding to wear her hair in the long curls she’d had at the charity gala the night they had first met, all that was needed was a pin the shape of a butterfly placed just above her left ear to expose the two piercings she had; a silver bar through the top of her ear and a twinkling stud in the lobe.

And if she’d flushed rather excessively at the memory of Oliver tugging on said stud with his tongue, drawing a gasp and moan from her throat, his hands hot on her waist and the stiff ridge of his arousal right between her thighs...

Well, she’d just need to apply more face powder to cover it up.

Felicity knew she should be more nervous, but strangely, she wasn’t. The prospect of a good meal and even better wine meant that she was actually looking forward to it, regardless of the company and the tiny matter of the fact she was only doing this to set someone up for a particularly bruising fall.

It was easy for her to compartmentalize it, mostly. To separate her physical attraction to the man in question from the potential for any kind of emotional or romantic connection, a connection that absolutely could not – and _would not_ – happen.  But she couldn’t deny that there was _some_ thing sparking between them, drawing them together….

It was the fact that she didn’t know what that _something_ was that worried her. That made her nervous. It was frustrating, and confusing, and made everything unnecessarily jumbled up and _messy_.

She didn’t like messy.

Except when it came to her apartment, where messy meant “lived in” and not “too many thoughts and feelings going around in my head that I can’t make sense of.”

Besides, it was just _dinner_. Nothing to make a song and dance about.

And she didn’t sing. Or dance.

So, really, there was nothing to make a fuss over, because it was just a meal.

It was _just_ a meal.

***

It hadn’t been just a meal.

At exactly 7:45pm, Oliver had called her. She’d jumped, startled by the sound of her cellphone buzzing to life on the coffee table; she’d scrambled to answer it, holding her shawl closed with one hand while she picked up the call with the other.

“Hey, beautiful,” was Oliver’s greeting, and _oh_ , didn’t that make her flood with a tingling pleasure, the kind that made her feel sixteen years old again.

She giggled, unable to stop herself.

He’d called her _beautiful_.

Nobody had called her beautiful since…well, since Ray. And her Mom, she guessed, but since Moms were _supposed_ to say stuff like that, she figured it didn’t count.

“Felicity?”

She started; she’d completely forgotten that he was there. Well, on the other end of the line. And obviously expecting her to say something back instead of just giggling like an idiotic schoolgirl.

“Oh! Oh, yes, um. Sorry. Hi,” she babbled, mentally kicking herself for getting lost in her own head… _again_. “Good evening.”

_Good evening?_

**_Good evening?_ **

She was going on a date with him, not making a business deal! What the hell was wrong with her?

“I mean, not good evening. Not that it’s _not_ a good evening, I mean, I’m going on a date with you so it’s obviously a _good_ _evening_ …”

“Felicity,” she could almost hear the smile in his voice, the steady way he pronounced the syllables of her name, slow and serious; she wondered if that cute dimple she liked was presenting itself in his right cheek. “ _Breathe_.”

“Oh. Yeah, okay,” Felicity forced herself to exhale, imagining herself letting go of her nervous energy; then she breathed deeply, in through her nose, out through her mouth. While she did this, Oliver was quiet, listening intently.

“Better now?” he asked, amusement still in his voice. “I don’t want you freaking out on me at dinner.”

“I won’t,” she promised. “I am completely calm. Cool as a cucumber. Cooler, in fact.”

“Good,” he said. “But I can promise that the wine will be very good, so you can use booze to calm your nerves if you’re still freaking out later.”

“Trying to get me drunk, Oliver?” she teased, hoping she sounded braver and bolder than she felt. She could still feel the ghostly imprint of his mouth on her bare thighs under her dress, and it was distracting, clouding her thoughts and making her head fuzzy. “It’s only 7:48!”

There was a creak on the other end of the line, like he was reclining in his chair. She definitely tried _very_ hard not to think about that long, hard-muscled body of his stretched out in whatever it was he was sitting in, bicep straining against the material of his shirt as he put one arm over his head.

Definitely tried.

Very hard.

Oliver seemed to consider what she’d said for moment, then replied, “Mmhmm. Well, you’ll just have to find out, won’t you? Which reminds me….we’re running late. Meet me outside your building in two minutes.”

Then he hung up on her.

 _Again_!

It was getting hard to figure out what was “aiming for a bit of mystery and intrigue” and what was him just being rude.

Still, Felicity patted down her curls one last time and sprang up from her chair, grasping her beaded clutch in one hand and shoving her phone into it while she adjusted her shawl around her bare shoulders. She took a deep breath, tottering a little in her heels, and made for the door, remembering to lock her apartment behind her.

Only just.

 _Focus, focus, focus_ , she told herself. _It’s just dinner. You’re going out with him because he likes you. You’ve been on dinner dates before. You can do this_.

And she could.

Until she saw the limo, shiny and black and gleaming, parked outside her building and looking like the most luxurious automobile (or, really, the most luxurious _anything_ ) that her street had ever seen.

Which it probably was.

_Holy frack._

Her mouth having dropped open like a goldfish, she could do nothing but stare for a full thirty seconds, blinking behind her contact lenses and thinking, _Holy cow._

_This is a life I could get used to._

Which was a very scary thought indeed, because – no. No, she was not going there. Absolutely not. That kind of thinking only lead to dangerous places and overstretched ambitions and broken hearts.

A sharp wind blew her hair away from her face as she met who she assumed was the driver of the limousine, a man dressed all in black with a pointed cap pulled low over his face. He nodded to her politely as he opened the passenger door and gestured for her to climb inside.

The interior was cool and dark, buttery-soft leather covering the seats and thick black shag carpet covering the floors, tickling the bare parts of her feet where her shoes sank easily into it. She thought she could hear music playing, the soft strings of a violin, but she didn’t see any speakers or a radio; they must have been concealed, hidden from the eyes of the passengers in order to enhance the atmosphere.

She wasn’t aware that she was completely silent, simply sitting in awe of the wonderful vehicle she had found herself in, until she heard the driver door slam shut and Oliver took her hand, a gesture of greeting. The coolness of the interior was a shocking contrast to the warmth of his skin and the sudden realization of another person’s body heat beside her.

“Overwhelmed?” he asked, not unkindly, looking at her with an interest she could only describe as _smitten_. Even in the semi-darkness, his eyes seemed to sparkle with a kind of untold mirth; a private joke that only he knew.

“It’s a lot,” Felicity admitted, biting her lip. “Not in a bad way! Really, it’s… _wow_.” She jiggled her knee nervously, the hand that Oliver wasn’t holding twitching in her lap, fidgeting with the hem of her dress. “I grew up in Vegas on a single mom’s paycheck and I guess I’m just not used to this kind of luxury.”

_Aaaand…oversharing. Well done, Felicity._

“Sorry,” Oliver said softly, and at this, Felicity frowned, a little puzzled.

“For what?”

“I wasn’t – I didn’t – I don’t want you to feel uncomfortable,” he eventually stammered, ducking his head to avoid looking in her eyes.

Impressive, really, since he was the one who’d practically dry-humped her in the QC elevator that afternoon.

But she guessed that everyone had things that made them embarrassed. Even Oliver Queen.

It was kind of nice.

“I’m not,” she assured him. “It’s just a lot to take in. I feel like a princess.”

“I’m glad,” Oliver replied. “That’s how I want you to feel.”

Felicity’s skin went warm at that; her heart seemed to race at ten times its normal speed, and she was suddenly thankful that she’d worn her hair down, the long curls forming a curtain between her and Oliver, keeping out his blissed-out gaze. They sat in silence as the limousine rode along the Starling City streets, barely making a noise. Instead, she listened to the violin music and the low purr of the engine, enjoying the moment for what it was.

They never let go of each other’s hands.

A few minutes later, they were pulling up; the driver opened the door for them, and Oliver released Felicity’s hand to climb out first.

She’d be lying if she hadn’t mourned the break in contact.

Then he was extending his hand again, and she took it gratefully as he helped her out of the car, putting a hand on her waist to steady her when she stumbled a little on the sidewalk, not expecting the transition from the low seating of the limo to the street outside to upset her balance. 

“You okay?” he murmured, low enough so that nobody else could hear him.

“I’m not made to climb out of cars,” Felicity said. “Evidently. Especially when I’m in heels.”

“I like the shoes,” Oliver commented. “But I promised you dinner, and I don’t know about you, but I’m starved. Shall we?”

“Yes,” Felicity said resolutely, her cheeks pink from the cold air and the warmth of Oliver’s presence next to her. “Yes, we shall.”

 ***

A third of the bottle of wine that had appeared on their table the moment they’d sat down was gone by the time they reached the main course.

Felicity had worried at first about drinking too much; she didn’t want Oliver to think she was some kind of alcoholic going through a midlife crisis at 22. But Oliver had been equally generous with his own glass, refilling it twice before they had even finished the appetizers.

And they were very, very delicious appetizers.

“This food,” Felicity said, gesturing emphatically with her fork in between mouthfuls of garlic chicken parmesan, “is the best food I have ever tasted. It’s even better than Big Belly Burger, and that is an achievement.”

Oliver was quieter than usual during the meal. Not that she’d ever really noticed him being _talkative_ – she hadn’t spent enough time with him for that, not yet – but he seemed content to let her do all the work, telling him about her job and her apartment and her beloved red Mini Cooper while he sat back and listened intently, his eyes almost never leaving her face.

It was nice, but it was also unsettling. She felt like she was being observed, too closely for her to feel entirely comfortable. She had a secret of her own, and she didn’t want to expose it.

So Oliver’s silence was both unnerving and welcoming.

“You’re probably sick of me talking, right?” Felicity joked just as she had made her way through half of her dessert. She’d been self-conscious at first, not wanting to seem like a pig if she ordered three full courses (plus there was the ever-present worry of bloating in such a tight, figure-hugging dress and looking pregnant was not her goal on a date like this), but at the end of the day she’d thrown caution to the wind and ordered one. “I mean, I talk too much. I know I do. It’s a habit I’m trying to break. Like drugs.”

Oliver raised an eyebrow at that.

“Not that I’m a drug addict,” she added soberly. “I mean, I did try a pot brownie in college once, but it was my first and only experimentation with narcotics. Mostly because I’m allergic to nuts and I barely got to experience the marijuana before my throat closed up….which is totally not sexy for a first date. Well, a second date. A third date? Is this our third date?”

“That depends,” Oliver said, leaning forward to rest his arms on the table, making his biceps bulge, straining the material of his suit. Felicity watched them with an air of fascination before she realized he hadn’t finished speaking. “Do you consider what we almost did this afternoon before Walter interrupted us as a second date?”

On instinct, Felicity flushed all over; she felt the beginnings of arousal stir within her at the very mention of that incident, of their frantic kissing against the wood panels and Oliver’s lips on her thighs...

She pushed her hair back from her face. “I don’t think it counts because we never finished.”

Then she promptly slammed her elbow into the table, hitting the handle of her fork in the process and sending it clattering to the floor, leaving a smear of chocolate on the tablecloth as it went.

Felicity felt her face heat up like it was over an open flame; she stared, bug-eyed, embarrassment flooding through her.

Oliver laughed, a bark of laughter that was loud enough to draw the attention of the couple at the next table over; he seemed to shake his head in disbelief, like a dog clearing water from its ears, a grin on his face that hopefully meant that he wasn’t as embarrassed by her outburst and clumsiness as she was.

“Felicity, you really are something else,” he commented. He spun his wine glass between his fingers, almost without realizing that he was doing it; there was no danger of spilling anything because the glass was almost empty, only the dregs clinging to the bottom.

“You’re not going to say that I’m not like other girls, I hope,” Felicity said. “Because there’s nothing wrong with other girls. Granted, I may be jealous of them sometimes, but…”

“But?” Oliver prompted, and she suddenly feared she’d say too much, if she replied. She thought of the kind of girls he was usually photographed with, the girls (women, really, though some of them were probably young enough to be girls still) with long legs and long hair, manicured nails and short shorts. Short everything, really, except most of the women he’d been seen with were the tall, long-limbed model type.

It was kind of depressing to think that she wasn’t like those girls, because she’d thought she was past the point where she wanted to be.

Perhaps not.

“Nothing,” she said quickly, trying to backtrack. “It’s…nothing.”

Just for something to do in the slightly awkward silence that followed, she bent down to pick up her fallen fork, wiping it on her napkin before diving right in and finishing her dessert, not looking up from her plate until it was time to pay the check.

Oliver must have thought her both rude _and_ greedy, but at that point she didn’t really care. She’d embarrassed herself, and let her insecurities get in the way of a lovely evening that she had actually been looking forward to.

 _Dammit, Smoak. Way to ruin the mood_ and _your self-esteem in one fell swoop._

But the way he pulled out her chair and kept his hand on her spine - a respectful distance from her ass, she may add - while he paid and gave his compliments to the maître d made her feel marginally better, and she was pink for an entirely different reason once they were outside and Oliver wrapped his arm fully around her waist, drawing her in, so that she was pressed along the side of his body like it had been specially made for her.

Her shoulders bare save the thin black shawl she’d wrapped around herself for the night, the cold wind bit at her skin under her dress, and she was grateful for Oliver’s warm, solid presence, if only for the extra body heat he provided. The walked aimlessly, not really heading in any particular direction, following the streets around each block in no particularly pattern and enjoying the silence save for the noise of traffic and the wind whooshing past their ears.

It reminded Felicity of their first night out together, on the motorcycle, and how they’d wandered around for over an hour in the early morning light, taking it all in, and just…. _being._ Two people exploring their possible interest in each other and having fun.

_Woah._

_Possible interest?_

_No, Sir._

_There is definitely none of….that._

_Not on my end of the bargain, anyway._

“What are you thinking about?” Oliver asked suddenly, breaking the silence for the first time since she’d nearly spilled her deepest insecurities over chocolate cheesecake at the restaurant.

“Huh?”

“You look like you’re thinking about something pretty hard,” he explained, his fingers spasming against her waist, as if wanting to reach for her and grip her tighter but not knowing if he should. “Care to share with the class?”

_Just how I’m scamming you into falling in love with me._

Felicity shrugged, shaking her head. “It’s nothing important.”

“Oh, come on, I’m pretty sure it’s not,” Oliver jested. “You’re a smart girl, Felicity. You went to MIT. You probably have thoughts that are more than _nothing_.”

She was going to say “ _It’s nothing_ ,” again, but what she said instead was, the words biting, “Don’t call me a girl.”

Oliver flinched, taken aback, and frowned.

“I just meant –“, Felicity started, but it didn’t seem appropriate for her to continue talking right that very minute, in case she said something else, so she closed her mouth with a _clack_ of her jaw and tried to give Oliver a reassuring smile. He didn’t return it.

_Frack._

_What now?_

As they passed a small gelato shop, the front windows bright with golden light that spilled from the open door, standing ajar, bringing with it the sound of laughter and merriment and shouted orders between customers and staff, Felicity turn her face to the storefront. The heat coming from the small store made her cold eyelids and cheeks feel that little bit warmer, and the noise from inside the packed store was welcoming and somehow comforting, and significantly less awkward than the tense silence that stretched between her and Oliver as they walked.

Despite the cold, she suddenly wanted ice cream.

Or maybe frozen yogurt, with strawberries, or blueberries, or lemon sorbet made with real lemons….

But she was still glued to Oliver’s side, and he’d looked visibly hurt at her outburst, so she didn’t think she had it in her to ask if they could retrace their steps and go inside.

“Are you cold?” Oliver asked softly after a few moments, his hand moving from her waist to her back, spanning the centre of it. Felicity tried, and failed, to suppress a shiver at his words; she opened her mouth to say that it was the sudden gust of wind that sent goosebumps rippling up her arms and neck, but Oliver was already unbuttoning the dark peacoat he was wearing, the brass buttons catching the lamplight from the lampposts along the sidewalk. He opened one side of it and silently offered it to her, his eyebrows raised in hopeful expectancy.

Despite herself, she gave a smile and grabbed the side of his coat, letting herself be wrapped up in it. The thick material was warm from his skin and soft as a blanket cocoon; it forced her even closer to Oliver, and she instinctively wrapped an arm around his waist, her head resting on his chest, the coat wrapped around them pulling them closer together, snug and content.

It didn’t make the awkwardness _completely_ go away, but it smoothed things out a little, and Felicity was able to breathe a little easier as the time passed and they just kept wandering, the sky black above them and pricked with sparkling stars.

When they stopped suddenly on a street corner, Felicity was confused; but then a food cart came into sight, manned by a tall man with a thick beard, and Felicity was stunned when Oliver greeted the man enthusiastically with a smile and rapid speech that definitely wasn’t English.

 _Well, that’s unexpected,_ she thought.   _I thought the only language Oliver knew was flirting._

Apparently, he’d been hiding his linguistic talents.

She listened to the conversation between the two men with half-interest, the low sounds going over her head completely; they were speaking so fast, their voices quiet, that she couldn’t make out a single word, not even to guess at what language it was they were speaking. Something Slavic, maybe, judging by the tone of their voices and the sharp sounds of some words, and the rolling syllables of others.

As if the quiet of the evening was being well and truly being broken, an unfamiliar voice shouted at them from someway down the street.

“Ollie! Hey, Ollie!”

Oliver turned, looking around at what Felicity probably guessed was the sound of his nickname. He realised his grip on her waist to raise a hand in a wave at someone coming up the street towards them. Felicity unfurled herself from his coat with some reluctance; instead, she pulled her shawl tighter around herself and folded her arms over her stomach, determined to conserve as much warmth as she could from his body and the material no longer wrapped around her. 

“Tommy, hi!” Oliver said, grinning all over his face, when the other man approached them. It was the most he’d smiled all evening. There was a sinking feeling in her stomach that she was the reason behind it. Felicity looked at the newcomer curiously, trying to place his face. He was tall, like Oliver, but dark-haired and more young-looking, more remnants of boyish roundness in his face than Oliver’s sharp cheekbones and clean jawline. She racked her brains, wondering why he seemed so familiar.

 _Tommy_. Where had she heard that name before?

“Felicity, this is Tommy Merlyn,” Oliver explained, cutting off her train of thought. “My oldest friend, and the worst influence on me of almost anyone I know. Tommy, this is Felicity, my….”

 _Girlfriend, girlfriend,_ say girlfriend!

 _Wait, do I_ want _him to say girlfriend? We’ve been on two dates!_

“….she’s my date,” Oliver finished, shuffling his weight from one foot to the other. His hand rested just above her elbow, his touch light as a feather; he gave her arm a slight squeeze as he added, “My very _beautiful_ date.”

And, Heaven help her, she blushed.

It wasn’t every day that you were called beautiful by Starling City’s most eligible bachelor twice in one evening.

But wait – Tommy _Merlyn_?

Of _course_.

He was the prodigal son of Malcolm Merlyn and his wife Rebecca, heir to Merlyn Global Group – and just as notorious as Oliver for shirking his responsibilities and partying hard. It made sense that they would be close; their parents moved in the same social circles. It would be weird if they _didn’t_ know each other.

It was still weird, though, and Felicity gave a polite, “Nice to meet you,” while her brain was firing in all different directions all at once.

There was a pause, and then the sound of heels clacking on the sidewalk alerted them to the presence of another person, a woman, carrying two small pots loaded with ice cream, each with a mini pink spoon sticking out of the frozen – though slowly melting – sweet treat.

“Ugh, I’m so sorry, the line was _ridiculously_ long, can you believe the amount of people wanting ice cream at 10 o’clock at night?”

Felicity’s stomach _dropped_.

Because Laurel Lance was engrossed in handing Tommy one of the servings of ice cream she carried, pecking him on the cheek before swiping a drop of melted ice cream from the edge of her own tub and licking it off her fingers.

“Uh, Ollie, this is – this is Laurel,” Tommy stammered. “She’s _my_ date.”

Felicity felt her intestines squirm horribly, her stomach squelching in that unpleasant way it did just before you were about to be sick.

And then she promptly staggered a few paces behind her to the nearest trashcan and _was_.

Laurel was _so_ going to pay for this.

But first, she had to get over the shock of seeing her with Tommy Merlyn, and she didn’t think she was capable of doing that with her head hanging over the edge of a trashcan.

Whoever said romance was dead?

**Notes for the Chapter:**

> DUN DUN DUN. 
> 
> *dramatic music* 
> 
> Would it make you feel better if I said that I’d planned to end the chapter this way MONTHS before? C’mon, guys, there’s a reason that Merlance is the second pairing in this fic! You didn’t think it’d be THAT easy, did you?
> 
> On a more serious note, I need to apologize for not updating this fic much sooner. I’ve been struggling with cycles of severe episodes of depression and anxiety since the new year - a good few months - and it’s made it really hard feel excited about writing - or about anything, really. I even pulled away from Arrow and the Olicity fandom for a while for a badly-needed break from the intensity of it all. I just haven’t been in a good headspace to write (or do much of anything, fandom-wise) and therefore this story has suffered, which is why it’s taken so long to bring you this chapter. I hope you understand, and that you will be patient with me while I find my footing again and give this fic the best of my abilities and focus.


End file.
